Ethyl Acetate → 2-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-6-nitro-phenylamine

Participants

Reaction Conditions

Reaction Steps

A solution containing 2-(2-chloro-ethoxy)-6-nitro-phenylamine (4.1 g, 19 mmol) and 3-(1H-indol-3-yl)-propylamine (7.1 g, 40.8 mmol) in anhydrous dimethylsulfoxide (50 ml) was heated at 60° C. for 12 hours. Ethyl acetate (200 ml) was added and the mixture was washed with saturated sodium bicarbonate (3×200 ml) and brine (200 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude product. Purification by chromatography (ethyl acetate:hexanes:2N ammonia methanol=25:25:1) afforded 4.6 g (68.9%) of the product as a yellowish red viscous oil; MS EI m/e 354 (M+).

Provenance & Evidence