Synthesis and Characterization of Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide Derivatives from Diazomethane and HCl

Document Type: Research Paper



Reaction of thionyl chloride with 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-
oxoquinoline-3-carboxylic acid 1 gave acid chloride 2. Compound 2 was reacted with
glycine and D-glutamic acid to afford 2-(7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-
dihydroquinoline-3-carbonyl) aminopantandioicacid 3a and 2-(7-chloro-1-cyclopropyl-6-
fluoro -4- oxo-1,4-dihydroquinoline-3-carbonyl)aminoaceticacid 3b. These compounds were
changed to chloromethyl ketone derivatives 5a-b from diazomethane and then HCl (g)in dry
diethyl ether.