NO131814B - - Google Patents
Download PDFInfo
- Publication number
- NO131814B NO131814B NO740034A NO740034A NO131814B NO 131814 B NO131814 B NO 131814B NO 740034 A NO740034 A NO 740034A NO 740034 A NO740034 A NO 740034A NO 131814 B NO131814 B NO 131814B
- Authority
- NO
- Norway
- Prior art keywords
- bromo
- diethylaminoethoxy
- nitro
- chloro
- methoxy
- Prior art date
Links
- -1 alkylene radical Chemical class 0.000 claims description 110
- 238000000034 method Methods 0.000 claims description 57
- 238000002360 preparation method Methods 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 150000001448 anilines Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JGWKKSUFCHGXDE-UHFFFAOYSA-N ClC=1C=C(C=C(C1OCCN(CC)CC)OC)[N+](=O)[O-] Chemical compound ClC=1C=C(C=C(C1OCCN(CC)CC)OC)[N+](=O)[O-] JGWKKSUFCHGXDE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- YRBNNGKRSMTSLV-UHFFFAOYSA-N 3-chloro-4-[2-(diethylamino)ethoxy]-5-methoxyaniline Chemical compound CCN(CC)CCOC1=C(Cl)C=C(N)C=C1OC YRBNNGKRSMTSLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 229960000583 acetic acid Drugs 0.000 description 28
- 239000000203 mixture Substances 0.000 description 24
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 239000012458 free base Substances 0.000 description 12
- GTQMCLXYDGAKML-UHFFFAOYSA-N 2-bromo-4-nitro-6-propoxyphenol Chemical compound BrC1=C(C(=CC(=C1)[N+](=O)[O-])OCCC)O GTQMCLXYDGAKML-UHFFFAOYSA-N 0.000 description 11
- ZLIUCKSKAZKFLO-UHFFFAOYSA-N 4-nitro-2-propoxyphenol Chemical compound CCCOC1=CC([N+]([O-])=O)=CC=C1O ZLIUCKSKAZKFLO-UHFFFAOYSA-N 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 239000003589 local anesthetic agent Substances 0.000 description 9
- ZVPTYZWBPLCFSO-UHFFFAOYSA-N 2-bromo-6-methoxy-4-nitrophenol Chemical compound COC1=CC([N+]([O-])=O)=CC(Br)=C1O ZVPTYZWBPLCFSO-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 8
- 229960003742 phenol Drugs 0.000 description 8
- 229960001309 procaine hydrochloride Drugs 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 230000000144 pharmacologic effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IZLVFLOBTPURLP-UHFFFAOYSA-N 2-Methoxy-4-nitrophenol Chemical compound COC1=CC([N+]([O-])=O)=CC=C1O IZLVFLOBTPURLP-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VMFRCGQFUKFYKD-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-ethoxyaniline Chemical compound CCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC VMFRCGQFUKFYKD-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XUIKECLBCZBUCM-UHFFFAOYSA-N 1,2-dipropoxybenzene Chemical compound CCCOC1=CC=CC=C1OCCC XUIKECLBCZBUCM-UHFFFAOYSA-N 0.000 description 4
- MMEJODNZUARTMS-UHFFFAOYSA-N 2-(2-bromo-4-nitro-6-propoxyphenoxy)-N,N-diethylethanamine Chemical compound BrC=1C=C(C=C(C1OCCN(CC)CC)OCCC)[N+](=O)[O-] MMEJODNZUARTMS-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- WJPDMLFUDQGNLG-UHFFFAOYSA-N 2-chloro-6-methoxy-4-nitrophenol Chemical compound COC1=CC([N+]([O-])=O)=CC(Cl)=C1O WJPDMLFUDQGNLG-UHFFFAOYSA-N 0.000 description 4
- DRQVJTZKYMECFJ-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-propoxyaniline Chemical compound CCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC DRQVJTZKYMECFJ-UHFFFAOYSA-N 0.000 description 4
- RYNFYPWJNRXYGG-UHFFFAOYSA-N 4-nitro-1,2-dipropoxybenzene Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1OCCC RYNFYPWJNRXYGG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 4
- NGAVLQZEBCIHII-UHFFFAOYSA-N 1,2-bis(phenylmethoxy)benzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1OCC1=CC=CC=C1 NGAVLQZEBCIHII-UHFFFAOYSA-N 0.000 description 3
- QZYDOKBVZJLQCK-UHFFFAOYSA-N 1,2-diethoxybenzene Chemical compound CCOC1=CC=CC=C1OCC QZYDOKBVZJLQCK-UHFFFAOYSA-N 0.000 description 3
- DWFAHQLZKCFEFI-UHFFFAOYSA-N 2-(2-bromo-6-methoxy-4-nitrophenoxy)-N,N-diethylethanamine Chemical compound BrC=1C=C(C=C(C1OCCN(CC)CC)OC)[N+](=O)[O-] DWFAHQLZKCFEFI-UHFFFAOYSA-N 0.000 description 3
- OSJADQJAYORFFF-UHFFFAOYSA-N 2-butoxy-4-nitrophenol Chemical compound CCCCOC1=CC([N+]([O-])=O)=CC=C1O OSJADQJAYORFFF-UHFFFAOYSA-N 0.000 description 3
- SMSKVMYGPCHDOP-UHFFFAOYSA-N 2-chloro-4-nitro-6-propoxyphenol Chemical compound ClC1=C(C(=CC(=C1)[N+](=O)[O-])OCCC)O SMSKVMYGPCHDOP-UHFFFAOYSA-N 0.000 description 3
- GIHYKBDWFSOKNN-UHFFFAOYSA-N 2-ethoxy-4-nitrophenol Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1O GIHYKBDWFSOKNN-UHFFFAOYSA-N 0.000 description 3
- XCKKGVCQHHFKOB-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-methoxyaniline Chemical compound CCN(CC)CCOC1=C(Br)C=C(N)C=C1OC XCKKGVCQHHFKOB-UHFFFAOYSA-N 0.000 description 3
- GUSZEBMESBWMGJ-UHFFFAOYSA-N 3-chloro-5-methoxy-2-nitrophenol Chemical compound COC1=CC(O)=C([N+]([O-])=O)C(Cl)=C1 GUSZEBMESBWMGJ-UHFFFAOYSA-N 0.000 description 3
- NYOZWCXZNLOVBB-UHFFFAOYSA-N 4-bromo-5-methoxy-2-nitrophenol Chemical compound COC1=CC(O)=C(C=C1Br)[N+]([O-])=O NYOZWCXZNLOVBB-UHFFFAOYSA-N 0.000 description 3
- STAAMFWKDIAVEO-UHFFFAOYSA-N 4-nitro-2-phenylmethoxyphenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 STAAMFWKDIAVEO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IAIKYWPFNZRZMG-UHFFFAOYSA-N 1,2-dibutoxy-4-nitrobenzene Chemical compound CCCCOC1=CC=C([N+]([O-])=O)C=C1OCCCC IAIKYWPFNZRZMG-UHFFFAOYSA-N 0.000 description 2
- GHKFGRVGAQYZNT-UHFFFAOYSA-N 1,2-dibutoxybenzene Chemical compound CCCCOC1=CC=CC=C1OCCCC GHKFGRVGAQYZNT-UHFFFAOYSA-N 0.000 description 2
- VICCBFJYGOMECC-UHFFFAOYSA-N 1,2-dihexoxy-4-nitrobenzene Chemical compound CCCCCCOC1=CC=C([N+]([O-])=O)C=C1OCCCCCC VICCBFJYGOMECC-UHFFFAOYSA-N 0.000 description 2
- XNBVDORAKLGCKG-UHFFFAOYSA-N 1,2-dihexoxybenzene Chemical compound CCCCCCOC1=CC=CC=C1OCCCCCC XNBVDORAKLGCKG-UHFFFAOYSA-N 0.000 description 2
- YFWBUVZWCBFSQN-UHFFFAOYSA-N 1,2-dimethoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C=C1OC YFWBUVZWCBFSQN-UHFFFAOYSA-N 0.000 description 2
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
- DYQMYINVJCKQEY-UHFFFAOYSA-N 2-bromo-4-nitro-6-octoxyphenol Chemical compound BrC1=C(C(=CC(=C1)[N+](=O)[O-])OCCCCCCCC)O DYQMYINVJCKQEY-UHFFFAOYSA-N 0.000 description 2
- WRYDGMWSKBGVHS-UHFFFAOYSA-N 2-bromo-n,n-diethylethanamine Chemical compound CCN(CC)CCBr WRYDGMWSKBGVHS-UHFFFAOYSA-N 0.000 description 2
- BWKZHGBUDZMPRZ-UHFFFAOYSA-N 2-chloro-5-ethoxy-4-nitrophenol Chemical compound ClC1=C(C=C(C(=C1)[N+](=O)[O-])OCC)O BWKZHGBUDZMPRZ-UHFFFAOYSA-N 0.000 description 2
- ZQXJTHSKSKQDQP-UHFFFAOYSA-N 2-fluoro-6-methoxy-4-nitrophenol Chemical compound COC1=CC(=CC(F)=C1O)[N+]([O-])=O ZQXJTHSKSKQDQP-UHFFFAOYSA-N 0.000 description 2
- MJRUICBEVVAILY-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-methoxyaniline;hydrochloride Chemical compound Cl.CCN(CC)CCOC1=C(Br)C=C(N)C=C1OC MJRUICBEVVAILY-UHFFFAOYSA-N 0.000 description 2
- VFNXIZZCTOSWRF-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-phenylmethoxyaniline Chemical compound CCN(CC)CCOC1=C(Br)C=C(N)C=C1OCC1=CC=CC=C1 VFNXIZZCTOSWRF-UHFFFAOYSA-N 0.000 description 2
- PJIHWXSQPSJVFM-UHFFFAOYSA-N 3-bromo-5-butoxy-4-[2-(diethylamino)ethoxy]aniline Chemical compound CCCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC PJIHWXSQPSJVFM-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- LRQBSZQPEWMHBA-UHFFFAOYSA-N 4-bromo-2-nitro-5-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC(O)=C(C=C1Br)[N+]([O-])=O LRQBSZQPEWMHBA-UHFFFAOYSA-N 0.000 description 2
- NHSCIOXOMBYZFC-UHFFFAOYSA-N 4-bromo-5-nitro-2-propoxyphenol Chemical compound C(CC)OC1=C(C=C(C(=C1)Br)[N+](=O)[O-])O NHSCIOXOMBYZFC-UHFFFAOYSA-N 0.000 description 2
- ZWEVOPCBFNUSMD-UHFFFAOYSA-N 4-nitro-1,2-bis(phenylmethoxy)benzene Chemical compound C=1C=CC=CC=1COC1=CC([N+](=O)[O-])=CC=C1OCC1=CC=CC=C1 ZWEVOPCBFNUSMD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- HWYNRVXFYFQSID-UHFFFAOYSA-M benzo[a]phenoxazin-9-ylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C1=CC=C2C(N=C3C=CC(C=C3O3)=[N+](C)C)=C3C=CC2=C1 HWYNRVXFYFQSID-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- OCNPXKLQSGAGKT-UHFFFAOYSA-N propyl benzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=CC=C1 OCNPXKLQSGAGKT-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- DTYUTSMRCQYVNW-UHFFFAOYSA-N 1,2-diethoxy-4-nitrobenzene Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1OCC DTYUTSMRCQYVNW-UHFFFAOYSA-N 0.000 description 1
- ZGKKCGFTZOZVIG-UHFFFAOYSA-N 1-(2-chloroethyl)-2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1CCCl ZGKKCGFTZOZVIG-UHFFFAOYSA-N 0.000 description 1
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 1
- HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 1
- SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 description 1
- DSTFFVLZNCFDLP-UHFFFAOYSA-N 2-(2-methoxy-4-nitrophenoxy)-n,n-dimethylethanamine Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OCCN(C)C DSTFFVLZNCFDLP-UHFFFAOYSA-N 0.000 description 1
- FESGGABAWWNIFM-UHFFFAOYSA-N 2-amino-6-methoxy-4-nitrophenol Chemical compound NC1=C(C(=CC(=C1)[N+](=O)[O-])OC)O FESGGABAWWNIFM-UHFFFAOYSA-N 0.000 description 1
- SCHXRTYYLATPNW-UHFFFAOYSA-N 2-bromo-4-butoxy-6-nitrophenol Chemical compound BrC1=C(C(=CC(=C1)OCCCC)[N+](=O)[O-])O SCHXRTYYLATPNW-UHFFFAOYSA-N 0.000 description 1
- FDPQBZXVKGFXGS-UHFFFAOYSA-N 2-bromo-4-methoxy-5-nitrophenol Chemical compound COC1=CC(Br)=C(O)C=C1[N+]([O-])=O FDPQBZXVKGFXGS-UHFFFAOYSA-N 0.000 description 1
- ULWBRWZMAAXUJG-UHFFFAOYSA-N 2-bromo-5-[2-(diethylamino)ethoxy]-4-methoxyaniline Chemical compound BrC1=C(N)C=C(C(=C1)OC)OCCN(CC)CC ULWBRWZMAAXUJG-UHFFFAOYSA-N 0.000 description 1
- BAADLJBNKVHGKS-UHFFFAOYSA-N 2-bromo-6-methoxy-3-nitrophenol Chemical compound COC1=CC=C([N+]([O-])=O)C(Br)=C1O BAADLJBNKVHGKS-UHFFFAOYSA-N 0.000 description 1
- QOHJWGXVMZSTAZ-UHFFFAOYSA-N 2-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CC(C)Cl QOHJWGXVMZSTAZ-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- FTVBULCXIBJLDX-UHFFFAOYSA-N 2-nitro-5-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=C([N+]([O-])=O)C(O)=C1 FTVBULCXIBJLDX-UHFFFAOYSA-N 0.000 description 1
- ZWKYKRVKMFGRSE-UHFFFAOYSA-N 3-(2-chloro-6-ethoxy-4-nitrophenoxy)-N,N-diethylpropan-1-amine hydrochloride Chemical compound Cl.ClC=1C=C(C=C(C1OCCCN(CC)CC)OCC)[N+](=O)[O-] ZWKYKRVKMFGRSE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XXCZNUYVSSRRAC-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-ethoxyaniline;hydrochloride Chemical compound [Cl-].CCOC1=CC([NH3+])=CC(Br)=C1OCCN(CC)CC XXCZNUYVSSRRAC-UHFFFAOYSA-N 0.000 description 1
- BFNZFLKBNYBARE-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-hexoxyaniline Chemical compound CCCCCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC BFNZFLKBNYBARE-UHFFFAOYSA-N 0.000 description 1
- WQQGHMNDOMWFLC-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-hexoxyaniline;dihydrochloride Chemical compound Cl.Cl.CCCCCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC WQQGHMNDOMWFLC-UHFFFAOYSA-N 0.000 description 1
- OZFDQHORRLUWED-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-phenylmethoxyaniline;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CCOC1=C(Br)C=C(N)C=C1OCC1=CC=CC=C1 OZFDQHORRLUWED-UHFFFAOYSA-N 0.000 description 1
- AFRZYLBAOTXPDM-UHFFFAOYSA-N 3-bromo-4-[2-(diethylamino)ethoxy]-5-propoxyaniline;dihydrochloride Chemical compound Cl.Cl.CCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC AFRZYLBAOTXPDM-UHFFFAOYSA-N 0.000 description 1
- IKCQLGJVAMDHIM-UHFFFAOYSA-N 3-bromo-5-butoxy-4-[2-(diethylamino)ethoxy]aniline;dihydrochloride Chemical compound Cl.Cl.CCCCOC1=CC(N)=CC(Br)=C1OCCN(CC)CC IKCQLGJVAMDHIM-UHFFFAOYSA-N 0.000 description 1
- DLQIXMCVXXWVPB-UHFFFAOYSA-N 3-chloro-4-[2-(diethylamino)ethoxy]-5-ethoxyaniline;hydrochloride Chemical compound Cl.CCOC1=CC(N)=CC(Cl)=C1OCCN(CC)CC DLQIXMCVXXWVPB-UHFFFAOYSA-N 0.000 description 1
- ZICOUZIFJOBVNX-UHFFFAOYSA-N 3-chloro-4-[2-(dimethylamino)ethoxy]-5-methoxyaniline;hydrochloride Chemical compound Cl.COC1=CC(N)=CC(Cl)=C1OCCN(C)C ZICOUZIFJOBVNX-UHFFFAOYSA-N 0.000 description 1
- SETUXQHZWZBATA-UHFFFAOYSA-N 3-chloro-4-[3-(diethylamino)propoxy]-5-ethoxyaniline;hydrochloride Chemical compound Cl.CCOC1=CC(N)=CC(Cl)=C1OCCCN(CC)CC SETUXQHZWZBATA-UHFFFAOYSA-N 0.000 description 1
- LZVYZZFCAMPFOQ-UHFFFAOYSA-N 3-chloro-5-methoxyphenol Chemical compound COC1=CC(O)=CC(Cl)=C1 LZVYZZFCAMPFOQ-UHFFFAOYSA-N 0.000 description 1
- NQCQVNHLNXCSPY-UHFFFAOYSA-N 3-chloropropyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCCl)C=C1 NQCQVNHLNXCSPY-UHFFFAOYSA-N 0.000 description 1
- ZUNWONPKZLVYCJ-UHFFFAOYSA-N 3-ethoxy-4-nitrophenol Chemical compound CCOC1=CC(O)=CC=C1[N+]([O-])=O ZUNWONPKZLVYCJ-UHFFFAOYSA-N 0.000 description 1
- WZVFUTFJQNFKST-UHFFFAOYSA-N 4-bromo-2-methoxy-5-nitrophenol Chemical compound COC1=CC(Br)=C([N+]([O-])=O)C=C1O WZVFUTFJQNFKST-UHFFFAOYSA-N 0.000 description 1
- RPYBYIOJISGHNI-UHFFFAOYSA-N 4-bromo-2-methoxy-6-nitrophenol Chemical compound COC1=CC(Br)=CC([N+]([O-])=O)=C1O RPYBYIOJISGHNI-UHFFFAOYSA-N 0.000 description 1
- BVTGNOGSGLFHGO-UHFFFAOYSA-N 4-chloro-5-methoxy-2-nitrophenol Chemical compound COC1=CC(O)=C([N+]([O-])=O)C=C1Cl BVTGNOGSGLFHGO-UHFFFAOYSA-N 0.000 description 1
- GLZWJURLFCQSQO-UHFFFAOYSA-N 4-chloro-n,n-diethylbutan-1-amine Chemical compound CCN(CC)CCCCCl GLZWJURLFCQSQO-UHFFFAOYSA-N 0.000 description 1
- OHSSWZLKWHLYFP-UHFFFAOYSA-N 5-bromo-2-hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC(O)=C(C=O)C=C1Br OHSSWZLKWHLYFP-UHFFFAOYSA-N 0.000 description 1
- FTJYIBROXYZBAG-UHFFFAOYSA-N 5-chloro-3-methoxy-2-nitrophenol Chemical compound COC1=CC(Cl)=CC(O)=C1[N+]([O-])=O FTJYIBROXYZBAG-UHFFFAOYSA-N 0.000 description 1
- CFCOQFMDDRKLLN-UHFFFAOYSA-N 5-nitro-2-propoxyphenol Chemical compound C(CC)OC1=C(C=C(C=C1)[N+](=O)[O-])O CFCOQFMDDRKLLN-UHFFFAOYSA-N 0.000 description 1
- QJYORGFWRDBDKR-UHFFFAOYSA-N 6-chloro-3-methoxy-2-nitrophenol Chemical compound COC1=CC=C(Cl)C(O)=C1[N+]([O-])=O QJYORGFWRDBDKR-UHFFFAOYSA-N 0.000 description 1
- VRQOTFOYJZJOHI-UHFFFAOYSA-N 6-iodo-3-methoxy-2-nitrophenol Chemical compound COC1=CC=C(I)C(O)=C1[N+]([O-])=O VRQOTFOYJZJOHI-UHFFFAOYSA-N 0.000 description 1
- SCIAAGPJPAELIH-UHFFFAOYSA-N BrC1=C(C=CC(=C1OCCN(CC)CC)OC)[N+](=O)[O-] Chemical compound BrC1=C(C=CC(=C1OCCN(CC)CC)OC)[N+](=O)[O-] SCIAAGPJPAELIH-UHFFFAOYSA-N 0.000 description 1
- QHNBHAHITLKCSI-UHFFFAOYSA-N BrC=1C=C(N)C=C(C1OCCN(CC)CC)OCCC(C)C Chemical compound BrC=1C=C(N)C=C(C1OCCN(CC)CC)OCCC(C)C QHNBHAHITLKCSI-UHFFFAOYSA-N 0.000 description 1
- PMCMWKXJXXIPLN-UHFFFAOYSA-N BrC=1C=C(N)C=C(C1OCCN(CC)CC)OCCCCCCCC Chemical compound BrC=1C=C(N)C=C(C1OCCN(CC)CC)OCCCCCCCC PMCMWKXJXXIPLN-UHFFFAOYSA-N 0.000 description 1
- YSLLLJFCSAXUGM-UHFFFAOYSA-N C(C)N(CCOC1=C(C=C(C(=C1)OC(C)C)Br)[N+](=O)[O-])CC Chemical compound C(C)N(CCOC1=C(C=C(C(=C1)OC(C)C)Br)[N+](=O)[O-])CC YSLLLJFCSAXUGM-UHFFFAOYSA-N 0.000 description 1
- PKHBAGFFTANPPT-UHFFFAOYSA-N C(C)N(CCOC1=C(C=C(C(=C1)OC)Cl)[N+](=O)[O-])CC Chemical compound C(C)N(CCOC1=C(C=C(C(=C1)OC)Cl)[N+](=O)[O-])CC PKHBAGFFTANPPT-UHFFFAOYSA-N 0.000 description 1
- YAIGSWQBSPIVCK-UHFFFAOYSA-N C(C)N(CCOC1=C(C=C(C(=C1)OC)I)[N+](=O)[O-])CC Chemical compound C(C)N(CCOC1=C(C=C(C(=C1)OC)I)[N+](=O)[O-])CC YAIGSWQBSPIVCK-UHFFFAOYSA-N 0.000 description 1
- ITAVNIHPBJAODB-UHFFFAOYSA-N C(C)N(CCOC1=C(C=C(C=C1Br)OCCCC)[N+](=O)[O-])CC Chemical compound C(C)N(CCOC1=C(C=C(C=C1Br)OCCCC)[N+](=O)[O-])CC ITAVNIHPBJAODB-UHFFFAOYSA-N 0.000 description 1
- DABZZGZOFBVTRG-UHFFFAOYSA-N C(C)N(CCOC1=C(C=C(C=C1OC)Br)[N+](=O)[O-])CC Chemical compound C(C)N(CCOC1=C(C=C(C=C1OC)Br)[N+](=O)[O-])CC DABZZGZOFBVTRG-UHFFFAOYSA-N 0.000 description 1
- IQAFAZMPDGJARN-UHFFFAOYSA-N C(C)N(CCOC1=C(N)C=C(C(=C1)OC(C)C)Br)CC Chemical compound C(C)N(CCOC1=C(N)C=C(C(=C1)OC(C)C)Br)CC IQAFAZMPDGJARN-UHFFFAOYSA-N 0.000 description 1
- ASFIDHFBYKOYQQ-UHFFFAOYSA-N C(C)N(CCOC1=C(N)C=C(C(=C1)OC)Br)CC Chemical compound C(C)N(CCOC1=C(N)C=C(C(=C1)OC)Br)CC ASFIDHFBYKOYQQ-UHFFFAOYSA-N 0.000 description 1
- ROCUXOZWDSJSJP-UHFFFAOYSA-N C(C)N(CCOC1=C(N)C=C(C(=C1)OC)I)CC Chemical compound C(C)N(CCOC1=C(N)C=C(C(=C1)OC)I)CC ROCUXOZWDSJSJP-UHFFFAOYSA-N 0.000 description 1
- TVGNKCDFLFEVQY-UHFFFAOYSA-N C(C)N(CCOC1=C(N)C=C(C=C1Br)OCCCC)CC Chemical compound C(C)N(CCOC1=C(N)C=C(C=C1Br)OCCCC)CC TVGNKCDFLFEVQY-UHFFFAOYSA-N 0.000 description 1
- SMKUDQSKFAJHDS-UHFFFAOYSA-N C(C)N(CCOC1=C(N)C=C(C=C1OC)Br)CC Chemical compound C(C)N(CCOC1=C(N)C=C(C=C1OC)Br)CC SMKUDQSKFAJHDS-UHFFFAOYSA-N 0.000 description 1
- ODDUPDASYUNSMW-UHFFFAOYSA-N CCCCN(CCCC)CCOC(C(OCCC)=CC([N+]([O-])=O)=C1)=C1Br Chemical compound CCCCN(CCCC)CCOC(C(OCCC)=CC([N+]([O-])=O)=C1)=C1Br ODDUPDASYUNSMW-UHFFFAOYSA-N 0.000 description 1
- MBTLYVQCYNVLRA-UHFFFAOYSA-N CCN(CC)CCOC(C(OC)=CC(N)=C1)=C1F Chemical compound CCN(CC)CCOC(C(OC)=CC(N)=C1)=C1F MBTLYVQCYNVLRA-UHFFFAOYSA-N 0.000 description 1
- NDWCGZYFAGKXPZ-UHFFFAOYSA-N COC1=C(N)C(=CC(=C1)Cl)OCCN(CC)CC Chemical compound COC1=C(N)C(=CC(=C1)Cl)OCCN(CC)CC NDWCGZYFAGKXPZ-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- YMARBQGRKIYVID-UHFFFAOYSA-N Cl.ClC=1C=C(C=C(C1OCCCN(CC)CC)OC)[N+](=O)[O-] Chemical compound Cl.ClC=1C=C(C=C(C1OCCCN(CC)CC)OC)[N+](=O)[O-] YMARBQGRKIYVID-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RIVDXSCYJISHLV-UHFFFAOYSA-N N,N-diethyl-2-(6-iodo-3-methoxy-2-nitrophenoxy)ethanamine Chemical compound C(C)N(CCOC1=C(C(=CC=C1I)OC)[N+](=O)[O-])CC RIVDXSCYJISHLV-UHFFFAOYSA-N 0.000 description 1
- WZGUPBCWNZOBQD-UHFFFAOYSA-N N-[3-bromo-4-[2-(diethylamino)ethoxy]-5-ethoxyphenyl]formamide Chemical compound BrC=1C=C(NC=O)C=C(C1OCCN(CC)CC)OCC WZGUPBCWNZOBQD-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- YAKYJYNTWFZMGM-UHFFFAOYSA-N [3-chloro-4-[3-(diethylamino)propoxy]-5-methoxyphenyl]azanium;chloride Chemical compound [Cl-].CCN(CC)CCCOC1=C(Cl)C=C([NH3+])C=C1OC YAKYJYNTWFZMGM-UHFFFAOYSA-N 0.000 description 1
- RYECZOFVKSMHES-UHFFFAOYSA-N [3-chloro-4-[3-(dimethylamino)propoxy]-5-methoxyphenyl]azanium;chloride Chemical compound [Cl-].COC1=CC([NH3+])=CC(Cl)=C1OCCCN(C)C RYECZOFVKSMHES-UHFFFAOYSA-N 0.000 description 1
- SFMDLWABHJVEMW-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=C(C(=C1)I)OC)O Chemical compound [N+](=O)([O-])C1=C(C=C(C(=C1)I)OC)O SFMDLWABHJVEMW-UHFFFAOYSA-N 0.000 description 1
- QALQXPDXOWOWLD-UHFFFAOYSA-N [N][N+]([O-])=O Chemical compound [N][N+]([O-])=O QALQXPDXOWOWLD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009704 beneficial physiological effect Effects 0.000 description 1
- TUCIXUDAQRPDCG-UHFFFAOYSA-N benzene-1,2-diol Chemical compound OC1=CC=CC=C1O.OC1=CC=CC=C1O TUCIXUDAQRPDCG-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- NIKBCKTWWPVAIC-UHFFFAOYSA-N butyl benzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1 NIKBCKTWWPVAIC-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- KTUVYMAZYSSBKC-UHFFFAOYSA-N hexyl benzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=CC=C1 KTUVYMAZYSSBKC-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MDUHKPRZIVINRA-UHFFFAOYSA-N n,n-diethyl-2-(3-nitrophenoxy)ethanamine Chemical compound CCN(CC)CCOC1=CC=CC([N+]([O-])=O)=C1 MDUHKPRZIVINRA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229940074355 nitric acid Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO740034A NO131814B (is) | 1974-01-07 | 1974-01-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO740034A NO131814B (is) | 1974-01-07 | 1974-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO131814B true NO131814B (is) | 1975-05-05 |
Family
ID=19881373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO740034A NO131814B (is) | 1974-01-07 | 1974-01-07 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO131814B (is) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000049863A1 (en) * | 1999-02-22 | 2000-08-31 | Sjaastad As | Baitmachine and device for controlling fishhook movement in a baitmachine |
-
1974
- 1974-01-07 NO NO740034A patent/NO131814B/no unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000049863A1 (en) * | 1999-02-22 | 2000-08-31 | Sjaastad As | Baitmachine and device for controlling fishhook movement in a baitmachine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO140381B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive arylpiperaziner | |
| JPS63258837A (ja) | １−フェニル−３−ナフタレニルオキシプロパンアミン類 | |
| PT90619B (pt) | Processo para a preparacao de compostos de piperazina | |
| CS196328B2 (en) | Method of preparing novel derivatives of 2-aroyl-3-phenyl-benzothiophene | |
| US4837235A (en) | Indole and indazole keto sulphones as leukotriene antagonists | |
| JPS60239458A (ja) | 新規化合物およびそれを含有する抗不整脈剤医薬組成物 | |
| EP0049779B1 (en) | 3-aminoindazole derivatives and process for preparation thereof | |
| JPH0772181B2 (ja) | ベンズイミダゾール誘導体 | |
| NO841426L (no) | Fenylaminobenzenalkanoler og fremgangsmaate for deres fremstilling | |
| NO131814B (is) | ||
| US5086070A (en) | 4-benzyl-1h-indoles and anti-arrthymic use thereof | |
| US3133075A (en) | Ring-tri-substituted-aniline derivatives | |
| US3076845A (en) | Ring-tri-substituted-n-(lower-alkanoyl) aniline derivatives and preparation thereof | |
| US4853408A (en) | 4-phenylpropyl-indoles having antiarythmic activity | |
| CA1072100A (en) | 3a,4,6,7-tetrahydro-3-phenyl-7-(phenylalkylene) thio-pyrano- (4,3-c) pyrazole-2(3h)-alkanamine and analogs | |
| JPS60120865A (ja) | 新規カルボスチリル誘導体 | |
| NO138250B (no) | Analogifremgangsmaate for fremstilling av farmakologisk aktive benzylaminer | |
| Lunsford et al. | Preparation of 4-Amino-1-butanols and Some Derivatives of Pharmacological Interest | |
| NO126914B (is) | ||
| MX2008002018A (es) | Derivados de aminoaril sulfonamida como ligandos funcionales del 5-ht6. | |
| Coan et al. | Antifungal Agents1 | |
| JPH01311076A (ja) | １―〔３―（４―ヒドロキシフェニル）１―ヒドロキシ１―プロピル〕ベンゼン誘導体 | |
| US5380722A (en) | Indole carboxamides | |
| Blicke et al. | The Preparation of Substituted 3-Piperidones1 | |
| FI62057C (fi) | Foerfarande foer framstaellning av nya substituerade diaminobensofenoner |