Iodoethane → HCID 9930685, compound

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Reaction Steps

8-[(Cyclohexyl)(ethyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared from 0.5 g of ethyl 8-cyclohexylamino-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate, 0.19 cm3 of iodoethane, 0.096 g of sodium hydride as a 60% dispersion in mineral oil and 10 cm3 of dimethylformamide. After treatment with 10 cm3 of water and 2 cm3 of 1N hydrochloric acid, the mixture was extracted 3 times with 20 cm3 of trichloromethane. The combined organic phases were washed 1 time with 20 cm3 of water, dried over magnesium sulphate and concentrated under reduced pressure (20 kPa) at a temperature around 40° C. 0.25 g of 8-[(cyclohexyl)(ethyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was obtained in the form of a yellow solid melting at about 230° C.

Provenance & Evidence