O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-methoxyquinoline

Participants

Reaction Steps

A mixture of 3-butyryl-4-chloro-8-methoxyquinoline (6.0 g, 023 mol) and o-toluidine (6.0 ml, 0.056 mol) in 1,4-dioxan (100 ml) was heated under reflux with stirring for 1 hour. The mixture was evaporated and chromatographed (silica gel, 2% methanol in dichloromethane) to give 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline as an oil which was isolated as the hydrochloride salt (2.12 g, 25.1%), m.p. 215°-217° by crystallisation from ethyl acetate and then recrystallisation from acetone.

Provenance & Evidence