2-Toluidine hydrochloride → SK&F 96079

Participants

Reaction Steps

2-Methyl-3-(2-chloroethyl)-4-chloro-8-methoxyquinoline (8.37 g, 31 mmol) and 2-methylaniline hydrochloride (4.45 g, 31 mmol) in 1-butanol (100 ml) were heated at reflux for 5 days, then the solvent evaporated, the crude product taken up in dichloromethane, washed with aqueous sodium bicarbonate, dried and evaporated. Chromatography (silica gel, 2% methanolic ammonia in dichloromethane) and recrystallisation from aqueous ethanol gave 1-(2-methylphenyl)-4-methyl-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline (2.04 g, 22 %), m.p. 182°-183°.

Provenance & Evidence