Synthesis of a novel analog of nalidixic acid: 1‐Ethyl‐1,4‐dihydro‐4‐oxo‐7‐(trifluororaethyl)‐1,8‐naphthyridine‐ 3‐carboxylic acid | Zendy

Singh Baldev | Zendy; Lesher George Y. | Zendy

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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 ).

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