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Synthesis of 1‐(2,4,6‐trichlorophenyl)‐3‐(3‐nitro‐ and 2‐chloro‐5‐nitroanilino)‐5‐pyrazolones
Author(s) -
Tracy David J.
Publication year - 1979
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.5570160637
Subject(s) - pyrazolones , chemistry , amidine , nitro , methanol , hydrochloride , nitrile , aryl , organic chemistry , medicinal chemistry , alkyl
A convenient one flask synthesis of 1‐aryl‐3‐nitroanilino‐5‐pyrazolones in yields of 60–65% is described. Synthesis involves initial reaction of ethyl 3‐ethoxy‐3‐iminopropionate hydrochloride and a nitroaniline in methanol producing an imidate ester. The imidate ester is then reacted with an arylhydrazine forming an amidine. The amidine is then cyclized with base.