IL107405A - Substituted-2, 3-dicarboxypyridinium nitrates and process for their production - Google Patents
Substituted-2, 3-dicarboxypyridinium nitrates and process for their productionInfo
- Publication number
- IL107405A IL107405A IL107405A IL10740593A IL107405A IL 107405 A IL107405 A IL 107405A IL 107405 A IL107405 A IL 107405A IL 10740593 A IL10740593 A IL 10740593A IL 107405 A IL107405 A IL 107405A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- nitrate
- substituted
- nitro
- Prior art date
Links
- -1 Substituted-2, 3-dicarboxypyridinium nitrates Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical group CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 claims description 21
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- HCCXJVFMLWNDDT-UHFFFAOYSA-O 5-ethylpyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.CCC1=C[NH+]=C(C(O)=O)C(C(O)=O)=C1 HCCXJVFMLWNDDT-UHFFFAOYSA-O 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- YTJUUQNLEGAFIZ-UHFFFAOYSA-O 5-(bromomethyl)pyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.OC(=O)C1=CC(CBr)=C[NH+]=C1C(O)=O YTJUUQNLEGAFIZ-UHFFFAOYSA-O 0.000 claims 1
- XXWYCKDGDFHJEG-UHFFFAOYSA-O 5-(chloromethyl)pyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.OC(=O)C1=CC(CCl)=C[NH+]=C1C(O)=O XXWYCKDGDFHJEG-UHFFFAOYSA-O 0.000 claims 1
- RQUJZZAMTTXUON-UHFFFAOYSA-O 5-(methoxymethyl)pyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.COCC1=C[NH+]=C(C(O)=O)C(C(O)=O)=C1 RQUJZZAMTTXUON-UHFFFAOYSA-O 0.000 claims 1
- FFCGEDQEJYTATD-UHFFFAOYSA-O 5-methylpyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.CC1=C[NH+]=C(C(O)=O)C(C(O)=O)=C1 FFCGEDQEJYTATD-UHFFFAOYSA-O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims 1
- 229940099990 ogen Drugs 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 abstract description 27
- 239000004009 herbicide Substances 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 7
- 230000002363 herbicidal effect Effects 0.000 abstract description 5
- 238000002955 isolation Methods 0.000 abstract description 5
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical class OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 16
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- WJOHTKIAQIBFIO-UHFFFAOYSA-N 3-ethylquinolin-8-ol Chemical compound OC1=CC=CC2=CC(CC)=CN=C21 WJOHTKIAQIBFIO-UHFFFAOYSA-N 0.000 description 6
- MTAVBTGOXNGCJR-UHFFFAOYSA-N 5-ethylpyridine-2,3-dicarboxylic acid Chemical compound CCC1=CN=C(C(O)=O)C(C(O)=O)=C1 MTAVBTGOXNGCJR-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 150000002823 nitrates Chemical class 0.000 description 5
- 238000005614 Skraup synthesis reaction Methods 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YQBHMTJCFQOJAB-UHFFFAOYSA-O pyridin-1-ium-1,2-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.OC(=O)C1=CC=CC=[N+]1C(O)=O YQBHMTJCFQOJAB-UHFFFAOYSA-O 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- ADDCHCYVJJYEHF-UHFFFAOYSA-O pyridin-1-ium-2,3-dicarboxylic acid;nitrate Chemical compound [O-][N+]([O-])=O.OC(=O)C1=CC=C[NH+]=C1C(O)=O ADDCHCYVJJYEHF-UHFFFAOYSA-O 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CGMJIXLCLAOYLR-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C1=NCCN1 CGMJIXLCLAOYLR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WFAULHLDTDDABL-UHFFFAOYSA-N Proxazole citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(CC)C1=NOC(CCN(CC)CC)=N1 WFAULHLDTDDABL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- XLABPPWWFVQMBZ-UHFFFAOYSA-O pyridin-1-ium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=[NH+]C=C1 XLABPPWWFVQMBZ-UHFFFAOYSA-O 0.000 description 1
- 238000007100 recyclization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003809 water extraction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/967,349 US5284955A (en) | 1992-10-28 | 1992-10-28 | Substituted-2,3-dicarboxypyridinium nitrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL107405A0 IL107405A0 (en) | 1994-01-25 |
| IL107405A true IL107405A (en) | 1998-01-04 |
Family
ID=25512672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL107405A IL107405A (en) | 1992-10-28 | 1993-10-26 | Substituted-2, 3-dicarboxypyridinium nitrates and process for their production |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5284955A (pt) |
| EP (1) | EP0601288B1 (pt) |
| JP (1) | JP3315219B2 (pt) |
| AT (1) | ATE238991T1 (pt) |
| BR (1) | BR9304381A (pt) |
| DE (1) | DE69332923T2 (pt) |
| IL (1) | IL107405A (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5861419A (en) | 1996-07-18 | 1999-01-19 | Merck Frosst Canad, Inc. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| US7271383B2 (en) * | 2004-08-11 | 2007-09-18 | Lexmark International, Inc. | Scanning system with feedback for a MEMS oscillating scanner |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6054305B2 (ja) * | 1979-08-14 | 1985-11-29 | 山本化学合成株式会社 | キノリン酸銅の製造法 |
| US4798619A (en) * | 1980-06-02 | 1989-01-17 | American Cyanamid Co. | 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents |
| US5122608A (en) * | 1990-12-19 | 1992-06-16 | American Cyanamid Company | Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids |
-
1992
- 1992-10-28 US US07/967,349 patent/US5284955A/en not_active Expired - Lifetime
-
1993
- 1993-09-10 DE DE69332923T patent/DE69332923T2/de not_active Expired - Fee Related
- 1993-09-10 EP EP93114565A patent/EP0601288B1/en not_active Expired - Lifetime
- 1993-09-10 AT AT93114565T patent/ATE238991T1/de not_active IP Right Cessation
- 1993-10-26 IL IL107405A patent/IL107405A/en not_active IP Right Cessation
- 1993-10-27 JP JP28986693A patent/JP3315219B2/ja not_active Expired - Fee Related
- 1993-10-27 BR BR9304381A patent/BR9304381A/pt not_active Application Discontinuation
-
1994
- 1994-02-02 US US08/190,825 patent/US5410062A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP3315219B2 (ja) | 2002-08-19 |
| JPH06234743A (ja) | 1994-08-23 |
| IL107405A0 (en) | 1994-01-25 |
| EP0601288A2 (en) | 1994-06-15 |
| DE69332923T2 (de) | 2004-05-19 |
| DE69332923D1 (de) | 2003-06-05 |
| EP0601288B1 (en) | 2003-05-02 |
| US5284955A (en) | 1994-02-08 |
| US5410062A (en) | 1995-04-25 |
| ATE238991T1 (de) | 2003-05-15 |
| BR9304381A (pt) | 1994-06-07 |
| EP0601288A3 (en) | 1994-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6061158B2 (ja) | ６−（７−（（１−アミノシクロプロピル）メトキシ）−６−メトキシキノリン−４−イルオキシ）−ｎ−メチル−１−ナフトアミド、またはそれの薬学的に許容される塩の合成中間体およびその使用 | |
| EP0388619B1 (en) | Method for the sequential oxidation of substituted quinolines to produce substituted-pyridine-2,3-dicarboxylic acids | |
| EP0331899B1 (en) | A method for the sequential oxidation of substituted-8-hydroxy-quinolines to produce substituted-pyridine-2,3-dicarboxylic acids | |
| US4816588A (en) | Method for the preparation of pyridine-2,3-dicarboxylic acids | |
| EP0601288B1 (en) | Substituted 2,3-dicarboxypyridinium nitrates | |
| US2963478A (en) | 4, 7-diamino-nu-aralkyl-2-aryl-6-pteridinecarboxamides | |
| CA2245080C (en) | Process for the preparation of heteroarylcarboxylic amides and esters | |
| EP0259687B1 (en) | Method for the preparation of pyridine-2,3-dicarboxylic acids | |
| US5371229A (en) | Method for the preparation of 2,3-pyridine-dicarboxylic acids and derivatives thereof | |
| EP0370686B1 (en) | A process for preparing quinolone carboxylic acid intermediates | |
| US6320053B1 (en) | Preparation of heteroarylcarboxamides | |
| EP0226558B1 (en) | Chemical intermediates and methods for their preparation | |
| US5122608A (en) | Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids | |
| Honda et al. | Syntheses of 3-nitro-2, 4, 6-trihydroxybenzamide and thiobenzamide derivatives as highly potent inhibitors of photosynthetic electron transport | |
| EP0388620A1 (en) | Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones | |
| US4552967A (en) | Process for the synthesis of intermediates in the preparation of diaminopyridines | |
| JP2864653B2 (ja) | ２―ヒドロキシニコチン酸誘導体の製造方法 | |
| RU2236409C1 (ru) | Способ получения 7-аминопиридо[1,2-а][1,3]бензимидазола | |
| KR930006948B1 (ko) | 아미드 유도체의 제조방법 | |
| KR870000723B1 (ko) | 페니실린 유도체의 제조방법 | |
| JPH0551368A (ja) | ベンゾアゾロン類の製造方法 | |
| MXPA99005368A (en) | Procedure and intermediaries for the manufacturing of piridine-2,3-dicarboxil compounds | |
| HK1000107B (en) | Method for the preparation of 2,3-pyridine-dicarboxylic acids and derivatives thereof | |
| SI8711595A8 (sl) | Postopek za pridobivanje hinolin-2.3-dikarbonske kisline | |
| IL92335A (en) | Intermediates for the preparation of quinolone carboxylic acids and the process for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |