2-Toluidine hydrochloride → 4,6-Dimethyl-1-o-tolyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

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Reaction Steps

2,8-Dimethyl-3-(2-chloroethyl)-4-chloroquinoline (7.63 g, 30 mmol) and 2-methylaniline hydrochloride (4.31 g, 30 mmol) in 1-butanol (100 ml) wereheated at reflux for 4 days, then the solvent evaporated, the crude producttaken 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)-4,6-dimethyl-2,3-dihydropyrrolo-[3,2-c]quinoline (1.95 g, 23%), m.p. 126°-128°.

Provenance & Evidence