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Synthesis of a novel analog of nalidixic acid: 1‐Ethyl‐1,4‐dihydro‐4‐oxo‐7‐(trifluororaethyl)‐1,8‐naphthyridine‐ 3‐carboxylic acid
Author(s) -
Singh Baldev,
Lesher George Y.
Publication year - 1983
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.5570200249
Subject(s) - chemistry , ethanol , ethyl ester , carboxylic acid , trifluoromethyl , nalidixic acid , thionyl chloride , carboxylate , medicinal chemistry , organic chemistry , chloride , antibiotics , biochemistry , alkyl , antibiotic resistance
Reaction of nalidixic acid ( 1 ) with thionyl chloride and subsequent treatment with ethanol gave a mixture of ethyl 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(trichloromethyl)‐1,8‐naphthyridine‐3‐carboxylate ( 3 ) and diethyl 1‐ethyl‐1,4‐dihydro‐4‐oxo‐1,8‐naphthyridine‐3,7‐dicarboxylate ( 4 ). Ethyl1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(trichloromethyl)‐1,8‐naphthyridine‐3‐carboxylate ( 3 ) was reacted with antimony pentafluoride to afford 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(trifluoromethyl)‐l,8‐naphthyridine‐3‐carboxylic acid ( 5 ).