SK140098A3 - Process for the preparation of 5-(substituted methyl)-2,3- -pyridinedicarboxylic acids - Google Patents
Process for the preparation of 5-(substituted methyl)-2,3- -pyridinedicarboxylic acids Download PDFInfo
- Publication number
- SK140098A3 SK140098A3 SK1400-98A SK140098A SK140098A3 SK 140098 A3 SK140098 A3 SK 140098A3 SK 140098 A SK140098 A SK 140098A SK 140098 A3 SK140098 A3 SK 140098A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- halogen
- substituted
- phenyl
- hydrogen
- Prior art date
Links
- -1 5-(substituted methyl)-2,3- -pyridinedicarboxylic acids Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 2
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- FSKRSJMYNXGUBM-UHFFFAOYSA-N 2,2,4-trimethylpentanenitrile Chemical compound CC(C)CC(C)(C)C#N FSKRSJMYNXGUBM-UHFFFAOYSA-N 0.000 claims 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 claims 1
- JPIJMXOJEHMTPU-UHFFFAOYSA-N 5-methylpyridine-2,3-dicarboxylic acid Chemical compound CC1=CN=C(C(O)=O)C(C(O)=O)=C1 JPIJMXOJEHMTPU-UHFFFAOYSA-N 0.000 claims 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229960003512 nicotinic acid Drugs 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical class OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 1
- BPPSPXOWNGOEGL-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)pyridine Chemical class N1CCN=C1C1=CC=CC=N1 BPPSPXOWNGOEGL-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZCDHDTQWOJRFFE-UHFFFAOYSA-N dimethyl 5-(methoxymethyl)pyridine-2,3-dicarboxylate Chemical compound COCC1=CN=C(C(=O)OC)C(C(=O)OC)=C1 ZCDHDTQWOJRFFE-UHFFFAOYSA-N 0.000 description 1
- MKOJTLPEGLTEFM-UHFFFAOYSA-N dimethyl 5-methylpyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(C)=CN=C1C(=O)OC MKOJTLPEGLTEFM-UHFFFAOYSA-N 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81252091A | 1991-12-20 | 1991-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK280477B6 SK280477B6 (sk) | 2000-02-14 |
| SK140098A3 true SK140098A3 (en) | 2000-02-14 |
Family
ID=25209833
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1400-98A SK140098A3 (en) | 1991-12-20 | 1992-12-15 | Process for the preparation of 5-(substituted methyl)-2,3- -pyridinedicarboxylic acids |
| SK3665-92A SK280466B6 (sk) | 1991-12-20 | 1992-12-15 | 5,6-disubstituované-3-pyridylmetylamóniumhalogenid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK3665-92A SK280466B6 (sk) | 1991-12-20 | 1992-12-15 | 5,6-disubstituované-3-pyridylmetylamóniumhalogenid |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5288866A (de) |
| EP (1) | EP0548532B1 (de) |
| JP (1) | JP3107672B2 (de) |
| KR (1) | KR100245586B1 (de) |
| AT (1) | ATE151752T1 (de) |
| AU (1) | AU652874B2 (de) |
| BR (1) | BR9205097A (de) |
| CA (1) | CA2085802C (de) |
| CZ (2) | CZ286513B6 (de) |
| DE (1) | DE69219089T2 (de) |
| DK (1) | DK0548532T3 (de) |
| ES (1) | ES2100261T3 (de) |
| GR (1) | GR3023303T3 (de) |
| HK (1) | HK1001055A1 (de) |
| HU (2) | HU217563B (de) |
| IL (1) | IL104134A (de) |
| MX (1) | MX9207270A (de) |
| SG (1) | SG47555A1 (de) |
| SK (2) | SK140098A3 (de) |
| TW (1) | TW222267B (de) |
| ZA (1) | ZA929877B (de) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0747360B1 (de) * | 1995-06-05 | 2001-09-19 | Basf Aktiengesellschaft | Verbessertes Verfahren zur Herstellung von 5-(Alkoxymethyl)-pyridin-2,3-dicarboxylat Salz |
| US5633380A (en) * | 1995-06-05 | 1997-05-27 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
| DK0798296T3 (da) * | 1996-03-21 | 2004-04-05 | Lonza Ag | Fremgangsmåde til fremstilling af arylamider af heteroaromatiske carboxylsyrer |
| SK283920B6 (sk) | 1996-03-28 | 2004-05-04 | Lonza Ag | Spôsob výroby arylamidov heteroaromatických karboxylových kyselín |
| EP0806415B1 (de) * | 1996-05-09 | 2000-02-16 | Lonza Ag | Verfahren zur Herstellung von Arylamiden heteroaromatischer Carbonsäuren |
| US5900484A (en) * | 1996-09-18 | 1999-05-04 | Lonza Ag | Process for the preparation of arylamides of heteroaromatic carboxylic acids |
| US5849916A (en) * | 1996-06-10 | 1998-12-15 | American Cyanamid Company | Process for the preparation of 2,3-pyridinedicarboximides |
| US6316629B1 (en) | 1997-06-10 | 2001-11-13 | American Cyanamid Co. | Process for the preparation of 2,3-pyridinedicarboximides |
| NZ314904A (en) * | 1996-06-10 | 1998-06-26 | American Cyanamid Co | Preparation of a herbicidal [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halide |
| US5905154A (en) * | 1996-06-10 | 1999-05-18 | American Cyanamid Company | Process for the preparation of 5-(alkoxymethyl)-2,3-pyridinedicarboximide compounds |
| PT820987E (pt) | 1996-07-23 | 2003-03-31 | Lonza Ag | Processo para a preparacao de esteres de acidos piridino-2,3-dicarboxilicos |
| CA2209392C (en) * | 1996-07-23 | 2007-02-20 | Yves Bessard | Process for preparing pyridinecarboxylic esters |
| US6172117B1 (en) | 1998-02-27 | 2001-01-09 | Akzo Nobel N.V. | Biocidal preservatives |
| DK1644333T3 (da) * | 2003-07-02 | 2010-01-18 | Basf Se | In-situ behandling af puridin-2,3-dicarboxylsyreestere med et oxidationsmiddel |
| US7795439B2 (en) * | 2004-06-25 | 2010-09-14 | Basf Aktiengesellschaft | In-situ treatment of pyridine 2,3-dicarboxylic acid esters with an oxidizing agent |
| SG132562A1 (en) | 2005-11-14 | 2007-06-28 | Agency Science Tech & Res | Nano-positioning electromagnetic linear actuator |
| US7941953B2 (en) * | 2006-01-17 | 2011-05-17 | Bedford Industries, Inc. | Separable composite labeling articles in sheet or roll form |
| UY32243A (es) * | 2008-11-13 | 2010-05-31 | Basf Se | Proceso para la fabricacion de bromuros de 3-piridilmetil amonio sustituidos |
| BRPI0922087B1 (pt) * | 2008-11-13 | 2018-02-14 | Basf Se | Processos para fabricar um composto e para preparar um composto |
| JP5619761B2 (ja) | 2008-11-13 | 2014-11-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ２−［（１−シアノプロピル）カルバモイル］−５−クロロメチルニコチン酸及びイミダゾリノン系除草剤の製造におけるその使用 |
| TWI506019B (zh) | 2008-12-08 | 2015-11-01 | Basf Se | 製造經取代５－甲氧基甲基吡啶－２，３－二羧酸衍生物之方法 |
| EP2376472B1 (de) | 2008-12-09 | 2015-08-19 | Basf Se | Verfahren zur herstellung von 5-formylpyridin-2,3-dicarbonsäureestern |
| EP3284847B1 (de) * | 2016-08-15 | 2019-01-02 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Korrosionsinhibitorzusammensetzung für magnesium oder magnesiumlegierungen |
| CA3227887C (en) * | 2016-11-21 | 2025-11-18 | Adama Agan Ltd. | PROCESS FOR PREPARING METHOXY METHYL PYRIDINE DICARBOXYLATE |
| EP3782985A1 (de) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Verfahren zur herstellung von 5-methoxymethylpyridin-2,3-dicarbonsäurederivaten |
| CN117024406A (zh) * | 2023-07-07 | 2023-11-10 | 江苏省农用激素工程技术研究中心有限公司 | 甲氧咪草烟的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5137889A (en) * | 1983-12-02 | 1992-08-11 | Otsuka Pharmaceutical Co., Ltd. | Dihydropyridine derivatives and process for preparing the same |
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
| US4748244A (en) * | 1984-05-11 | 1988-05-31 | Ciba-Geigy Corporation | Process for the preparation of pyridine-2-3-dicarboxylic acid derivatives, and novel 1-amino-1,4-dihydropyridine-2-3-diarboxylic acid derivatives |
| GB8602518D0 (en) * | 1986-02-01 | 1986-03-05 | Wyeth John & Brother Ltd | 1 4-dihydropyridines |
| GB2192877A (en) * | 1986-07-22 | 1988-01-27 | Shell Int Research | Herbicidal imidazolinyl compounds |
| JPH0625116B2 (ja) * | 1987-07-08 | 1994-04-06 | ダイソー株式会社 | ピリジン−２，３−ジカルボン酸誘導体の製造法 |
| MY104933A (en) * | 1987-09-30 | 1994-07-30 | Pfizer Ltd | Platelet activating factor antagonists |
| DE3914969A1 (de) * | 1989-05-02 | 1990-11-08 | Schering Ag | 5-substituierte 3-arylisoxazol-derivate, deren herstellung und verwendung als schaedlingsbekaempfungsmittel |
| US5262384A (en) * | 1989-10-10 | 1993-11-16 | Basf Aktiengesellschaft | Pyridine derivatives and their use for controlling undesirable plant growth |
| EP0461401A1 (de) * | 1990-06-15 | 1991-12-18 | American Cyanamid Company | Verfahren zur Herstellung von 2,3-Pyridindicarbonsäure-dialkylestern aus Dialkyldichloromaleinsäureestern |
| US5125961A (en) * | 1991-08-12 | 1992-06-30 | Monsanto Company | Substituted pyridine compounds |
-
1992
- 1992-10-14 US US07/960,749 patent/US5288866A/en not_active Expired - Lifetime
- 1992-11-16 EP EP92119537A patent/EP0548532B1/de not_active Expired - Lifetime
- 1992-11-16 AT AT92119537T patent/ATE151752T1/de active
- 1992-11-16 SG SG1996002817A patent/SG47555A1/en unknown
- 1992-11-16 DE DE69219089T patent/DE69219089T2/de not_active Expired - Lifetime
- 1992-11-16 DK DK92119537.6T patent/DK0548532T3/da active
- 1992-11-16 ES ES92119537T patent/ES2100261T3/es not_active Expired - Lifetime
- 1992-11-26 TW TW081109493A patent/TW222267B/zh not_active IP Right Cessation
- 1992-12-15 SK SK1400-98A patent/SK140098A3/sk not_active IP Right Cessation
- 1992-12-15 CZ CS19923665A patent/CZ286513B6/cs not_active IP Right Cessation
- 1992-12-15 MX MX9207270A patent/MX9207270A/es unknown
- 1992-12-15 SK SK3665-92A patent/SK280466B6/sk not_active IP Right Cessation
- 1992-12-16 JP JP04353923A patent/JP3107672B2/ja not_active Expired - Lifetime
- 1992-12-17 IL IL104134A patent/IL104134A/xx not_active IP Right Cessation
- 1992-12-18 BR BR9205097A patent/BR9205097A/pt not_active IP Right Cessation
- 1992-12-18 HU HU9204021A patent/HU217563B/hu unknown
- 1992-12-18 AU AU30280/92A patent/AU652874B2/en not_active Expired
- 1992-12-18 ZA ZA929877A patent/ZA929877B/xx unknown
- 1992-12-18 CA CA002085802A patent/CA2085802C/en not_active Expired - Lifetime
- 1992-12-18 HU HU9602838A patent/HU218004B/hu unknown
- 1992-12-19 KR KR1019920024795A patent/KR100245586B1/ko not_active Expired - Lifetime
-
1993
- 1993-11-22 US US08/156,205 patent/US5378843A/en not_active Expired - Lifetime
-
1994
- 1994-11-04 US US08/334,297 patent/US5545835A/en not_active Expired - Lifetime
-
1997
- 1997-04-09 CZ CZ19971082A patent/CZ286519B6/cs not_active IP Right Cessation
- 1997-05-02 GR GR960403251T patent/GR3023303T3/el unknown
-
1998
- 1998-01-05 HK HK98100065A patent/HK1001055A1/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK140098A3 (en) | Process for the preparation of 5-(substituted methyl)-2,3- -pyridinedicarboxylic acids | |
| KR940001774B1 (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
| SK48393A3 (en) | Process for the preparation of pyrimidine compounds | |
| CA3248246A1 (en) | PROCESS FOR PREPARING A PYRROL COMPOUND AND AN INTERMEDIATE THEREOF | |
| JPH04230263A (ja) | ピリジンジカルボン酸化合物の製法 | |
| RU2090558C1 (ru) | 5,6-дизамещенные 3-пиридилметиламмоний галогениды, способ их получения и способы получения 5-(замещенный метил)-2,3-пиридиндикарбоновых кислот | |
| RU2117007C1 (ru) | Способ получения 2-замещенных 4,6-диалкоксипиримидинов,2-n-бутиламино-4,6-диметоксипиримидин и способ получения галогенпроизводных пиримидина | |
| SK284852B6 (sk) | Spôsob výroby pyridín-2,3-dikarboxylátových zlúčenín a ich medziprodukty | |
| JP2524491B2 (ja) | 新規なアミノカルボン酸エステル及びその製法 | |
| DK163184B (da) | Fremgangsmaade til fremstilling af 2-carbamoyl-nicotin- og -3-quinolincarboxylsyrer | |
| EP1038861B1 (de) | 4-fluoro-3-oxocarbonsäureester und ihre herstellung | |
| JP3243072B2 (ja) | ２，５−二置換ピリジン類の製造方法 | |
| JPH02289563A (ja) | ｏ―カルボキシピリジル―およびｏ―カルボキシキノリルイミダゾリノンの改良製造法 | |
| JP2002535311A (ja) | マロノニトリル及びアセトンからの３‐アミノ−２−クロロ−４‐メチルピリジンの合成 | |
| IE62321B1 (en) | New process for the synthesis of the alpha-(1-methylethyl)-3,4-dimethoxybenzeneacetonitrile | |
| SK154294A3 (en) | Method of production of 2,4,5-tribrompyrole-3-carbonitrile | |
| IE900028A1 (en) | "New process for separating optical isomers of 1,4-dihydropyridine derivatives" | |
| JP4449211B2 (ja) | ６−（１−フルオロエチル）−５−ヨード−４−ピリミドン及びその製法 | |
| KR100262747B1 (ko) | 할로말레인산 및 할로푸마르산 에스테르의 제조방법 | |
| JP3982645B2 (ja) | Ｎ−置換ジオキソチアゾリジルベンズアミド誘導体の製造中間体 | |
| US5886223A (en) | Process for the preparation of substituted β-ketoanilide compounds | |
| JP4055246B2 (ja) | ５−クロロ−６−（α−フルオロアルキル）−４−ピリミドン及びその製法 | |
| JPS5857370A (ja) | ４−アミノ−２−ピペラジニルピリミジン誘導体及びその製造法 | |
| HU218980B (hu) | Eljárás 5-(alkoxi-metil)-2,3-piridin-dikarboximid-származékok és ezekből herbicid hatású imidazolinonszármazékok előállítására és az eljárás köztitermékei | |
| CZ289952B6 (cs) | Substituované chinolinové deriváty |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20121215 |