AU637277B2 - Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids - Google Patents
Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids Download PDFInfo
- Publication number
- AU637277B2 AU637277B2 AU89858/91A AU8985891A AU637277B2 AU 637277 B2 AU637277 B2 AU 637277B2 AU 89858/91 A AU89858/91 A AU 89858/91A AU 8985891 A AU8985891 A AU 8985891A AU 637277 B2 AU637277 B2 AU 637277B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- pyridine
- quinolinedicarboxylic
- water
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical class C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 34
- -1 quinolinedicarboxylic acid diester Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 230000007062 hydrolysis Effects 0.000 claims abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 6
- CJSGMWRJOBFTCK-UHFFFAOYSA-N 5-(methoxymethyl)pyridine-2,3-dicarboxylic acid Chemical compound COCC1=CN=C(C(O)=O)C(C(O)=O)=C1 CJSGMWRJOBFTCK-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000011874 heated mixture Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 1
- 229960005215 dichloroacetic acid Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000002955 isolation Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- VSPXTWXXNZJEHM-UHFFFAOYSA-N diethyl 5-ethylpyridine-2,3-dicarboxylate Chemical compound CCOC(=O)C1=CC(CC)=CN=C1C(=O)OCC VSPXTWXXNZJEHM-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 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 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 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 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical class C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004611 spectroscopical analysis 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
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)
- Quinoline Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/631,594 US5122608A (en) | 1990-12-19 | 1990-12-19 | Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids |
| US631594 | 1990-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8985891A AU8985891A (en) | 1992-06-25 |
| AU637277B2 true AU637277B2 (en) | 1993-05-20 |
Family
ID=24531896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU89858/91A Ceased AU637277B2 (en) | 1990-12-19 | 1991-12-18 | Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5122608A (en:Method) |
| EP (1) | EP0491140B1 (en:Method) |
| JP (1) | JPH04295466A (en:Method) |
| KR (1) | KR100198166B1 (en:Method) |
| AT (1) | ATE151072T1 (en:Method) |
| AU (1) | AU637277B2 (en:Method) |
| BR (1) | BR9105447A (en:Method) |
| CA (1) | CA2057787A1 (en:Method) |
| DE (1) | DE69125461T2 (en:Method) |
| DK (1) | DK0491140T3 (en:Method) |
| ES (1) | ES2099728T3 (en:Method) |
| GR (1) | GR3023302T3 (en:Method) |
| HU (1) | HU208956B (en:Method) |
| IE (1) | IE914432A1 (en:Method) |
| IL (1) | IL99882A (en:Method) |
| PT (1) | PT99816B (en:Method) |
| SG (1) | SG47574A1 (en:Method) |
| TW (1) | TW198713B (en:Method) |
| ZA (1) | ZA919958B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208342A (en) * | 1992-03-30 | 1993-05-04 | Hoechst Celanese Corporation | Conversion of pyridine-2,3-dicarboxylic acid esters to cyclic anhydrides |
| US5284955A (en) * | 1992-10-28 | 1994-02-08 | American Cyanamid Company | Substituted-2,3-dicarboxypyridinium nitrates |
| ES2709063T3 (es) * | 2016-08-15 | 2019-04-15 | Helmholtz Zentrum Geesthacht | Composición inhibidora de la corrosión para magnesio o aleaciones de magnesio |
| EP3782985A1 (en) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR880375A (fr) * | 1940-07-26 | 1943-03-24 | Ig Farbenindustrie Ag | Procédé pour préparer à partir de leurs esters des acides carboxyliques de la série pyridique |
| GB880592A (en) * | 1959-03-16 | 1961-10-25 | Koppers Co Inc | Improvements in or relating to pyridine carboxylic acid preparation |
| US3027380A (en) * | 1959-06-10 | 1962-03-27 | Lilly Co Eli | Process for preparing 5-fluoronicotinic acid |
| BE788353A (fr) * | 1972-07-26 | 1973-01-02 | Labofina Sa | Procede d'oxydation de la quinoleine |
| US3829432A (en) * | 1973-04-02 | 1974-08-13 | Labofina Sa | Process for the oxidation of quinoline |
| 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 |
| DE3150005A1 (de) * | 1981-12-17 | 1983-06-23 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur herstellung von chinolinsaeure |
| US4460776A (en) * | 1982-05-25 | 1984-07-17 | American Cyanamid Company | Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters |
| US4656283A (en) * | 1982-05-25 | 1987-04-07 | American Cyanamid Company | Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid |
| US4608079A (en) * | 1983-08-02 | 1986-08-26 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| DE3345223A1 (de) * | 1983-12-14 | 1985-06-27 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur herstellung von chinolinsaeure aus chinolin |
| US4723011A (en) * | 1985-10-28 | 1988-02-02 | American Cyanamid Company | Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters |
| DE3882055T2 (de) * | 1987-01-06 | 1993-12-02 | Sugai Chemical Ind Co Ltd | Verfahren zur Herstellung von Pyridin-2,3-dicarboxylsäure-Verbindungen. |
| US4847405A (en) * | 1987-03-19 | 1989-07-11 | American Cyanamid Company | Method for the preparation of anilinofumarate [quinoline-2,3- dicarboxylic] |
| GB8709228D0 (en) * | 1987-04-16 | 1987-05-20 | Shell Int Research | Preparation of heterocyclic 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 |
-
1990
- 1990-12-19 US US07/631,594 patent/US5122608A/en not_active Expired - Lifetime
-
1991
- 1991-10-24 AT AT91118108T patent/ATE151072T1/de not_active IP Right Cessation
- 1991-10-24 ES ES91118108T patent/ES2099728T3/es not_active Expired - Lifetime
- 1991-10-24 DE DE69125461T patent/DE69125461T2/de not_active Expired - Fee Related
- 1991-10-24 SG SG1996002900A patent/SG47574A1/en unknown
- 1991-10-24 DK DK91118108.9T patent/DK0491140T3/da active
- 1991-10-24 EP EP91118108A patent/EP0491140B1/en not_active Expired - Lifetime
- 1991-10-29 IL IL9988291A patent/IL99882A/en not_active IP Right Cessation
- 1991-11-05 TW TW080108702A patent/TW198713B/zh active
- 1991-12-13 BR BR919105447A patent/BR9105447A/pt not_active IP Right Cessation
- 1991-12-16 JP JP3352728A patent/JPH04295466A/ja active Pending
- 1991-12-16 PT PT99816A patent/PT99816B/pt not_active IP Right Cessation
- 1991-12-17 CA CA002057787A patent/CA2057787A1/en not_active Abandoned
- 1991-12-18 KR KR1019910023377A patent/KR100198166B1/ko not_active Expired - Fee Related
- 1991-12-18 ZA ZA919958A patent/ZA919958B/xx unknown
- 1991-12-18 IE IE443291A patent/IE914432A1/en not_active IP Right Cessation
- 1991-12-18 AU AU89858/91A patent/AU637277B2/en not_active Ceased
- 1991-12-18 HU HU914008A patent/HU208956B/hu not_active IP Right Cessation
-
1997
- 1997-05-02 GR GR960403250T patent/GR3023302T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW198713B (en:Method) | 1993-01-21 |
| PT99816A (pt) | 1992-12-31 |
| AU8985891A (en) | 1992-06-25 |
| EP0491140B1 (en) | 1997-04-02 |
| KR100198166B1 (ko) | 1999-06-15 |
| IL99882A (en) | 1995-05-26 |
| KR920012034A (ko) | 1992-07-25 |
| HU914008D0 (en) | 1992-03-30 |
| DE69125461D1 (de) | 1997-05-07 |
| PT99816B (pt) | 1999-05-31 |
| CA2057787A1 (en) | 1992-06-20 |
| BR9105447A (pt) | 1992-08-25 |
| DE69125461T2 (de) | 1997-07-17 |
| DK0491140T3 (da) | 1997-04-21 |
| US5122608A (en) | 1992-06-16 |
| ZA919958B (en) | 1992-10-28 |
| IE914432A1 (en) | 1992-07-01 |
| IL99882A0 (en) | 1992-08-18 |
| JPH04295466A (ja) | 1992-10-20 |
| ATE151072T1 (de) | 1997-04-15 |
| GR3023302T3 (en) | 1997-08-29 |
| HUT59670A (en) | 1992-06-29 |
| ES2099728T3 (es) | 1997-06-01 |
| HU208956B (en) | 1994-02-28 |
| SG47574A1 (en) | 1998-04-17 |
| EP0491140A1 (en) | 1992-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |