JPH0135825B2 - - Google Patents
Info
- Publication number
- JPH0135825B2 JPH0135825B2 JP55076827A JP7682780A JPH0135825B2 JP H0135825 B2 JPH0135825 B2 JP H0135825B2 JP 55076827 A JP55076827 A JP 55076827A JP 7682780 A JP7682780 A JP 7682780A JP H0135825 B2 JPH0135825 B2 JP H0135825B2
- Authority
- JP
- Japan
- Prior art keywords
- toluoyl
- methyl
- acetic acid
- pyrrole
- carboxypyrrole
- 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.)
- Expired
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YASSGZAFJWNSPO-UHFFFAOYSA-N 2-(carboxymethyl)-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)CC=1NC=CC=1C(O)=O YASSGZAFJWNSPO-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000013078 crystal Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QLLUGZYSTABSKS-UHFFFAOYSA-N 2-(carboxymethyl)-1-methyl-5-(4-methylbenzoyl)pyrrole-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(C(O)=O)=C(CC(O)=O)N1C QLLUGZYSTABSKS-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 1-methyl-5-(p-toluoyl)-3-ethoxycarbonylpyrrole-2-ethyl acetate Chemical compound 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HOPPBOBZKTVAEA-UHFFFAOYSA-N 2-[3-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid Chemical compound C1(=CC=C(C=C1)C(=O)C1=C(NC=C1)CC(=O)O)C HOPPBOBZKTVAEA-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- WIDHUKOADYLKIO-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylate Chemical compound CCOC(=O)CC1=C(C(=O)OCC)C=CN1C WIDHUKOADYLKIO-UHFFFAOYSA-N 0.000 description 1
- OIQILCRLOSXOMN-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-4-methyl-5-(4-methylbenzoyl)-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(CC(=O)OCC)NC(C(=O)C=2C=CC(C)=CC=2)=C1C OIQILCRLOSXOMN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RFLLKFAICZHHBA-UHFFFAOYSA-M sodium 2-(1H-pyrrol-2-yl)acetate dihydrate Chemical compound [Na+].O.O.N1C(=CC=C1)CC(=O)[O-] RFLLKFAICZHHBA-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7682780A JPS572270A (en) | 1980-06-06 | 1980-06-06 | Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid |
| CA000379120A CA1151187A (en) | 1980-06-06 | 1981-06-05 | Process for preparing 1-methyl-5-(p-toluoyl)pyrrole-2- acetic acid |
| AT253581A AT374794B (de) | 1980-06-06 | 1981-06-05 | Verfahren zur herstellung von 1-methyl-5(p-toluoyl)-pyrrol-2-essigsaeure |
| AT265783A AT375343B (de) | 1980-06-06 | 1983-07-20 | Verfahren zur herstellung der neuen 1-methyl-5(p-toluoyl)-3-carboxypyrrol-2-essigsaeure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7682780A JPS572270A (en) | 1980-06-06 | 1980-06-06 | Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572270A JPS572270A (en) | 1982-01-07 |
| JPH0135825B2 true JPH0135825B2 (da) | 1989-07-27 |
Family
ID=13616503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7682780A Granted JPS572270A (en) | 1980-06-06 | 1980-06-06 | Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS572270A (da) |
| AT (1) | AT374794B (da) |
| CA (1) | CA1151187A (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0230110A1 (en) * | 1985-11-30 | 1987-07-29 | FISONS plc | Pharmacologically active pyrrole and pyrazole derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4947752A (da) * | 1972-03-24 | 1974-05-09 |
-
1980
- 1980-06-06 JP JP7682780A patent/JPS572270A/ja active Granted
-
1981
- 1981-06-05 CA CA000379120A patent/CA1151187A/en not_active Expired
- 1981-06-05 AT AT253581A patent/AT374794B/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4947752A (da) * | 1972-03-24 | 1974-05-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| AT374794B (de) | 1984-05-25 |
| ATA253581A (de) | 1983-10-15 |
| CA1151187A (en) | 1983-08-02 |
| JPS572270A (en) | 1982-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH05208978A (ja) | １，２−ジヒドロ−３Ｈ−ピロロ〔１，２−α〕ピロール−１−カルボン酸エステルの５位のアロイル化方法 | |
| JP2575781B2 (ja) | ２，３−ジアシルオキシ−４−ヒドロキシ−トペンタナールおよびその製造方法 | |
| JPH0135825B2 (da) | ||
| JP3544727B2 (ja) | ２，４，５−トリブロモピロール−３−カルボニトリルの調製方法 | |
| JPH058200B2 (da) | ||
| JPH06293700A (ja) | ６−クロロサリチル酸の製造法 | |
| JPS5817461B2 (ja) | ブチロフェノン誘導体の製造法 | |
| JP2769058B2 (ja) | シクロプロパン誘導体の製法 | |
| JPS6353984B2 (da) | ||
| JP3233806B2 (ja) | スルフェニル酢酸誘導体の製造法 | |
| JP3272340B2 (ja) | １−［（シクロペント−３−エン−１−イル）メチル］−５−エチル−６−（３，５−ジメチルベンゾイル）−２，４−ピリミジンジオンの製造方法 | |
| JPS63216890A (ja) | チユアンシンマイシン類縁体の製造方法 | |
| JPS5852995B2 (ja) | フルフラ−ル誘導体の製造法 | |
| JPS5840541B2 (ja) | ３− チカン −２（ １ ｈ ） ピリドン −６− カルボンサンノ セイホウ | |
| JP2001158774A (ja) | ６−トリフルオロメチルニコチン酸類の製造方法 | |
| JPS649987B2 (da) | ||
| JPS649986B2 (da) | ||
| JPS58118566A (ja) | 新規な複素環式酢酸誘導体とその製法 | |
| JPH0527617B2 (da) | ||
| JPS5846513B2 (ja) | ２↓−アロイルホルミル置換ピロ−ル誘導体及びその製造方法 | |
| JPS6034538B2 (ja) | ２−クロル−２−ヒドロキシイミノ酢酸アルキルエステルの合成法 | |
| JPH05132478A (ja) | 新規な（１，３−ジチオラン−２−イリデン）メチル フエニルアルカン酸誘導体 | |
| JPH05339191A (ja) | アルデヒド類の製造法 | |
| JPH06742B2 (ja) | インド−ル誘導体の製造方法 | |
| JPH06166655A (ja) | テトラメトキシメチルベンズアルデヒドの製造方法 |