Sodium Hydroxide → 1-methyl-1H-indol-5-amine

Participants

Reaction Steps

To 1-methyl-5-nitro-1H-indole (0.5 g, 2.84 mmol) in ethyl acetate (10 ml), tin (II) chloride hydrate (2.5 g, 11.4 mmol, 4 eq) was added and the reaction mixture stirred overnight at room temperature. The reaction mixture was basified with aqueous sodium hydroxide solution (pH 8) and the compound extracted using ethyl acetate. The crude compound obtained was purified by column chromatography over silica gel using ethyl acetate/hexane (1:1) as eluent to give 1-methyl-1H-indol-5-ylamine (120 mg, 27%).

Provenance & Evidence