Non‐Steroidal antiinflammatory agents.  1 . A novel synthesis of 1‐methyl‐5‐ p ‐tolylpyrrole‐2‐acetic acid (tolmetin) | Zendy

Artico Marino | Zendy; Corelli Federico | Zendy; Massa Silvio | Zendy; Stefancich Giorgio | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research