CZ485289A3 - Process for preparing dialkyloxalacetate - Google Patents
Process for preparing dialkyloxalacetate Download PDFInfo
- Publication number
- CZ485289A3 CZ485289A3 CS894852A CS485289A CZ485289A3 CZ 485289 A3 CZ485289 A3 CZ 485289A3 CS 894852 A CS894852 A CS 894852A CS 485289 A CS485289 A CS 485289A CZ 485289 A3 CZ485289 A3 CZ 485289A3
- Authority
- CZ
- Czechia
- Prior art keywords
- quinoline
- preparation
- toluene
- quot
- hours
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 13
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 150000005690 diesters Chemical class 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- SHLFJVZPNLKZRX-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)quinoline-3-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N=C1C1=NCCN1 SHLFJVZPNLKZRX-UHFFFAOYSA-N 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- XQRVITDMGTWTIC-VURMDHGXSA-N (Z)-2-anilinobut-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)/NC1=CC=CC=C1 XQRVITDMGTWTIC-VURMDHGXSA-N 0.000 description 4
- XSCRWBSKSVOZOK-UHFFFAOYSA-N 2,3-dichlorobutanedioic acid Chemical compound OC(=O)C(Cl)C(Cl)C(O)=O XSCRWBSKSVOZOK-UHFFFAOYSA-N 0.000 description 4
- -1 5-oxo-2-imidazolin-2-yl Chemical group 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- PBGMSGHICSEALQ-UHFFFAOYSA-N diethyl 2,3-dichlorobutanedioate Chemical compound CCOC(=O)C(Cl)C(Cl)C(=O)OCC PBGMSGHICSEALQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical class C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- WFVKIANRKSZMGB-UHFFFAOYSA-N 2,2-diethoxyacetic acid Chemical compound CCOC(C(O)=O)OCC WFVKIANRKSZMGB-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- PBHUSRBVKLAGGU-UHFFFAOYSA-N 2-carbamoylquinoline-3-carboxylic acid Chemical class C1=CC=C2C=C(C(O)=O)C(C(=O)N)=NC2=C1 PBHUSRBVKLAGGU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- STDJOEKKLFKIEN-UHFFFAOYSA-N C(#CC(=O)OC(C)=O)C(=O)OC(C)=O Chemical class C(#CC(=O)OC(C)=O)C(=O)OC(C)=O STDJOEKKLFKIEN-UHFFFAOYSA-N 0.000 description 1
- MEFXSOGPINXQFU-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.C(C)C(C)(NCC)CC Chemical compound C(\C=C/C(=O)O)(=O)O.C(C)C(C)(NCC)CC MEFXSOGPINXQFU-BTJKTKAUSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NLDBQMDFKNDJBR-UHFFFAOYSA-N acetic acid;diethyl oxalate Chemical compound CC(O)=O.CCOC(=O)C(=O)OCC NLDBQMDFKNDJBR-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- ROMURMXNNUEGCC-BENRWUELSA-N diethyl (z)-2-anilinobut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)/NC1=CC=CC=C1 ROMURMXNNUEGCC-BENRWUELSA-N 0.000 description 1
- APQXANZCSQHHQW-UHFFFAOYSA-N diethyl 2-chloro-3-(diethylamino)butanedioate Chemical compound CCOC(=O)C(Cl)C(N(CC)CC)C(=O)OCC APQXANZCSQHHQW-UHFFFAOYSA-N 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 1
- 229940071094 diethyl oxalacetate Drugs 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/44—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
-
- 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Quinoline Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/902,275 US4766218A (en) | 1986-08-29 | 1986-08-29 | Method for the preparation of quinoline-2,3-dicarboxylic acid |
| US06/902,274 US4675432A (en) | 1986-08-29 | 1986-08-29 | Method for the preparation of anilinofumarate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ279233B6 CZ279233B6 (cs) | 1995-02-15 |
| CZ485289A3 true CZ485289A3 (en) | 1995-02-15 |
Family
ID=27129323
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS894852A CZ485289A3 (en) | 1986-08-29 | 1987-08-26 | Process for preparing dialkyloxalacetate |
| CS876238A CZ279232B6 (cs) | 1986-08-29 | 1987-08-26 | Způsob přípravy anilinofumarátu a od něho odvozené kyseliny chinolin-2,3-dikarboxylové |
| CS894853A CZ485389A3 (en) | 1986-08-29 | 1987-08-26 | Process for preparing aniline fumarate |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS876238A CZ279232B6 (cs) | 1986-08-29 | 1987-08-26 | Způsob přípravy anilinofumarátu a od něho odvozené kyseliny chinolin-2,3-dikarboxylové |
| CS894853A CZ485389A3 (en) | 1986-08-29 | 1987-08-26 | Process for preparing aniline fumarate |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0262305B1 (enExample) |
| JP (3) | JP2703540B2 (enExample) |
| KR (1) | KR960000759B1 (enExample) |
| AR (1) | AR243864A1 (enExample) |
| AT (1) | ATE57912T1 (enExample) |
| AU (1) | AU598023B2 (enExample) |
| BG (3) | BG49938A3 (enExample) |
| BR (1) | BR8704403A (enExample) |
| CA (1) | CA1293509C (enExample) |
| CZ (3) | CZ485289A3 (enExample) |
| DE (1) | DE3765899D1 (enExample) |
| ES (1) | ES2019335B3 (enExample) |
| GR (1) | GR3001037T3 (enExample) |
| HU (1) | HU206086B (enExample) |
| IE (1) | IE60928B1 (enExample) |
| IL (1) | IL83539A (enExample) |
| IN (1) | IN169438B (enExample) |
| SK (1) | SK278128B6 (enExample) |
| YU (2) | YU46225B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814486A (en) * | 1987-10-01 | 1989-03-21 | American Cyanamid Company | Method for the preparation of anilinofumarate |
| US4904816A (en) * | 1989-06-15 | 1990-02-27 | American Cyanamid Company | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof |
| US5405987A (en) * | 1989-08-31 | 1995-04-11 | Hoechst Celanese Corporation | Process for preparing pyridine and quinoline derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH560193A5 (enExample) * | 1968-06-14 | 1975-03-27 | Ciba Geigy Ag | |
| SE7908597L (sv) * | 1978-10-19 | 1980-04-20 | Mallinckrodt Inc | Sett att framstella ketosyror och -estrar |
| US4638068A (en) * | 1981-04-09 | 1987-01-20 | American Cyanamid Company | 2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| US4459409A (en) * | 1982-05-25 | 1984-07-10 | American Cyanamid Company | Process for the preparation of 2,3-quinolinedicarboxylic acids |
-
1987
- 1987-06-16 EP EP87108676A patent/EP0262305B1/en not_active Expired - Lifetime
- 1987-06-16 ES ES87108676T patent/ES2019335B3/es not_active Expired - Lifetime
- 1987-06-16 DE DE8787108676T patent/DE3765899D1/de not_active Expired - Fee Related
- 1987-06-16 AT AT87108676T patent/ATE57912T1/de not_active IP Right Cessation
- 1987-06-18 IN IN477/CAL/87A patent/IN169438B/en unknown
- 1987-08-08 BG BG082991A patent/BG49938A3/xx unknown
- 1987-08-12 CA CA000544303A patent/CA1293509C/en not_active Expired - Lifetime
- 1987-08-14 IL IL83539A patent/IL83539A/xx not_active IP Right Cessation
- 1987-08-26 CZ CS894852A patent/CZ485289A3/cs not_active IP Right Cessation
- 1987-08-26 CZ CS876238A patent/CZ279232B6/cs not_active IP Right Cessation
- 1987-08-26 CZ CS894853A patent/CZ485389A3/cs not_active IP Right Cessation
- 1987-08-26 SK SK6238-87A patent/SK278128B6/sk unknown
- 1987-08-27 BR BR8704403A patent/BR8704403A/pt not_active IP Right Cessation
- 1987-08-27 AR AR87308550A patent/AR243864A1/es active
- 1987-08-27 JP JP62211492A patent/JP2703540B2/ja not_active Expired - Lifetime
- 1987-08-28 YU YU159587A patent/YU46225B/sh unknown
- 1987-08-28 IE IE231187A patent/IE60928B1/en not_active IP Right Cessation
- 1987-08-28 BG BG081053A patent/BG48571A3/xx unknown
- 1987-08-28 KR KR1019870009564A patent/KR960000759B1/ko not_active Expired - Fee Related
- 1987-08-28 HU HU873796A patent/HU206086B/hu not_active IP Right Cessation
- 1987-08-28 AU AU77676/87A patent/AU598023B2/en not_active Ceased
-
1988
- 1988-02-15 BG BG082990A patent/BG47345A3/xx unknown
- 1988-09-23 YU YU179288A patent/YU46265B/sh unknown
-
1990
- 1990-11-01 GR GR90400313T patent/GR3001037T3/el unknown
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1996
- 1996-02-14 JP JP8051033A patent/JP2788221B2/ja not_active Expired - Lifetime
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1997
- 1997-12-26 JP JP9366588A patent/JP2842441B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20040826 |