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Conversion of the carboxyl group to the corresponding trichloromethyl group in the quinoline series
Author(s) -
Takahashi Kazuyuki,
Mitsuhashi Keiryo
Publication year - 1977
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.5570140531
Subject(s) - chemistry , thionyl chloride , phosphorus pentachloride , quinoline , steric effects , chloride , ring (chemistry) , medicinal chemistry , group (periodic table) , carboxylic acid , organic chemistry , nitrogen , methyl group
Various substituted quinaldinic acids were treated with phosphorus pentachloride in an excess of thionyl chloride. Carboxyl groups of quinaldinic acid, 6‐methyl‐, 6‐chloro‐, 4‐phenyl‐ and 4‐( p ‐chlorophenyl)quinaldinic acids and benzo[ f ]quinoline‐3‐carboxylic acid were converted to the trichloromethyl group, while those of 8‐methyl‐, 4‐(3,4‐dichlorophenyl)‐, 4‐(p‐nitrophenyl)‐quinaldinic acids and benzo[ h ]quinoline‐2‐carboxylic acid were not. The difference is discussed on the basis of the effects of the basicity of ring nitrogen and steric factors.