JPS572270A - Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid - Google Patents

Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid

Info

Publication number
JPS572270A
JPS572270A JP7682780A JP7682780A JPS572270A JP S572270 A JPS572270 A JP S572270A JP 7682780 A JP7682780 A JP 7682780A JP 7682780 A JP7682780 A JP 7682780A JP S572270 A JPS572270 A JP S572270A
Authority
JP
Japan
Prior art keywords
methyl
toluoyl
acetic acid
formula
compound
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.)
Granted
Application number
JP7682780A
Other languages
Japanese (ja)
Other versions
JPH0135825B2 (en
Inventor
Hiroaki Kinugasa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dainippon Pharmaceutical Co Ltd
Janssen Pharmaceuticals Inc
Original Assignee
Dainippon Pharmaceutical Co Ltd
McNeilab Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dainippon Pharmaceutical Co Ltd, McNeilab Inc filed Critical Dainippon Pharmaceutical Co Ltd
Priority to JP7682780A priority Critical patent/JPS572270A/en
Priority to CA000379120A priority patent/CA1151187A/en
Priority to AT253581A priority patent/AT374794B/en
Publication of JPS572270A publication Critical patent/JPS572270A/en
Priority to AT265783A priority patent/AT375343B/en
Publication of JPH0135825B2 publication Critical patent/JPH0135825B2/ja
Granted legal-status Critical Current

Links

Abstract

PURPOSE: To prepare the titled compound useful as an analgesic and antiphlogistic agent, in high yield, by heating 1-methyl-5-(p-toluoyl)-3-carboxypyrrole-2-acetic acid (novel compound) in the presence of a base.
CONSTITUTION: p-Toluoyl chloride of formula III is made to react with 1-methyl- 3-ethoxy-carbonylpyrrole-2-acetic acid ethyl ester in a solvent such as ethylene chloride in the presence of a Lewis acid such as AlCl3 at 0W90°C, and the resulted compound of formula V is hydrolyzed, e.g. by heating in a solvent such as hydrated ethanol in the presence of a base such as KOH to obtain 1-methyl-5-(p-toluoyl)- 3-carboxypyrrole-2-acetic acid of formula II which is a novel compound. The novel compound of formula II is converted to the objective compound of formula I by heating at 180W200°C for 1W4hr under pressure in the presence of a base such as aqueous ammonia, triethylamine, etc.
COPYRIGHT: (C)1982,JPO&Japio
JP7682780A 1980-06-06 1980-06-06 Preparation of 1-methyl-5- p-toluoyl pyrrole-2-acetic acid Granted JPS572270A (en)

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 (en) 1980-06-06 1981-06-05 METHOD FOR PRODUCING 1-METHYL-5 (P-TOLUOYL) -PYRROL-2-ACETIC ACID
AT265783A AT375343B (en) 1980-06-06 1983-07-20 METHOD FOR PRODUCING THE NEW 1-METHYL-5 (P-TOLUOYL) -3-CARBOXYPYRROL-2-ACETIC ACID

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 true JPS572270A (en) 1982-01-07
JPH0135825B2 JPH0135825B2 (en) 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 (en)
AT (1) AT374794B (en)
CA (1) CA1151187A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4947752A (en) * 1972-03-24 1974-05-09

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4947752A (en) * 1972-03-24 1974-05-09

Also Published As

Publication number Publication date
CA1151187A (en) 1983-08-02
ATA253581A (en) 1983-10-15
JPH0135825B2 (en) 1989-07-27
AT374794B (en) 1984-05-25

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