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

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.