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. Their conversions to the 7-Chloro-1-cyclopropyl-N-[5-diazo-1-(diazoacetyl)-4-oxopantyl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide 4a and 7-Chloro-1-cyclopropyl-N3-(diazo-2-oxopropyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide 4b were achieved under diazomethylation. These compounds were changed to cheloromethyl ketone derivatives 5a-b by using of HCl (g) in dry diethyl ether.