3-Methylpyridine → 7-(3-Aminomethyl-4-methyl-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

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A mixture of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), β-picoline (11 ml) and 3-aminomethyl-4-methylpyrrolidine (0.5 g) was refluxed for 8.5 hours, then the reacting mixture was cooled to room temperature. To the mixture was added concentrated aqueous ammonia (100 ml) and concentrated under reduced pressure. To the residue was added dichloromethane-ether (1:3, 37 ml), the resulting precipitate was collected by filtration, washed with ethanol-ether (1:3), recrystallized from ethanol and further recrystallized from chloroform-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.14 g) as pale yellow powder, mp 245°-248° C.

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