Acetic Acid → 2-(3,5-Dimethylphenyl)-1H-indol-5-amine

Participants

Reaction Steps

To a stirred solution of 2-(3,5-dimethylphenyl)-5-nitro-1H-indole (2 g in a mixture of 55 mL tetrahydrofuran and 20 mL methanol) was added 347 mg of 10% palladium hydroxide on carbon catalyst followed by acetic acid (1 mL of a 30% solution in water). The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 25 hours the flask was charged with an additional 320 mg catalyst and 1 mL of 30% acetic acid and re-subjected to hydrogen. After a total reaction time of 3 days, the mixture was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (hexane:ethyl acetate, 1:1) gave the title compound (1.16 g).

Provenance & Evidence