2,4-Dichloroaniline → 4-[(2,4-Dichlorophenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrile

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Reaction Steps

A mixture of 4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile (262 mg, 1.0 mmol), 2,4-dichloroaniline (195 mg, 1.2 mmol) and pyridine hydrochloride (140 mg, 1.2 mmol) in 10 mL of 2-ethoxyethanol is heated at reflux for 30 minutes. The reaction mixture is cooled to room temperature partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with a 1:1 mixture of saturated sodium bicarbonate and 5 N sodium hydroxide. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by column chromatography, eluting with a gradient of 1:1 ethyl acetate:hexane to all ethyl acetate provides 103 mg of 4-[(2,4-dichlorophenyl)amino]-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 144-145° C.

Provenance & Evidence