2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine → 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine

Participants

Reaction Steps

Under a nitrogen atmosphere, acetonitrile (2 L) was added to a Parr vessel containing 5% platinum on carbon (2.0 g) and 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitroquinolin-4-amine (36.12 g, 90.58 mmol). The vessel was sealed, purged with nitrogen, and placed under hydrogen pressure (30 psi, 2.1×105 Pa) for 17 hours at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting semi-solid was treated with diethyl ether, which was removed under reduced pressure to provide 33 g of 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine as a yellow-orange solid. A portion of the material was purified by column chromatography on silica gel (6 g, eluting with 10% ethyl acetate in hexane) to provide 0.0298 g of an analytically pure sample as pale yellow crystals, mp 127-128.0° C.

Provenance & Evidence