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Non‐Steroidal antiinflammatory agents. 1 . A novel synthesis of 1‐methyl‐5‐ p ‐tolylpyrrole‐2‐acetic acid (tolmetin)
Author(s) -
Artico Marino,
Corelli Federico,
Massa Silvio,
Stefancich Giorgio
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190647
Subject(s) - chemistry , acetic acid , pummerer rearrangement , hydrolysis , sulfoxide , acetic anhydride , formylation , methyl acetate , organic chemistry , condensation , medicinal chemistry , alkaline hydrolysis , catalysis , physics , thermodynamics
A four‐step preparation of 1‐methyl‐5‐ p ‐totylpyrrole‐2‐acetic acid (Tolmetin) is reported starting from 1‐methyl‐2‐ p ‐tolylpyrrole. Formylation of this compound followed by condensation with methyl(methylthio)‐methyl sulfoxide furnished 1‐(methylsulfinyl)‐1‐methylthio‐2‐(1‐methyl‐5‐ p ‐tolyl‐2‐pyrrolyl)ethylene. Pummerer rearrangement of the latter compound gave ethyl 1‐methyl‐5‐ p ‐tolylpyrrole‐2‐acetate, which was hydrolyzed in alkaline medium to afford Tolmetin.