3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

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Reaction Steps

An amount of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile (7.1 g, 26.9 mmol), and 3-chloro-4-fluoro-phenylamine (3.9 g, 26.8 mmol), were stirred in 2-propanol (70 mL), and heated at reflux for 2 hours. The mixture was cooled to room temperature and stirred for an additional 20 hours. The reaction mixture was evaporated to dryness, stirred with ethyl acetate and saturated sodium bicarbonate solution. After separation of the layers, the organic layer was washed with saturated brine solution and dried on magnesium sulfate, to give a dark green powder (9.9 g, 99%), which was used without further purification.

Provenance & Evidence