7-bromo-5-nitro-1H-indole → 7-Bromo-1H-indol-5-amine

Participants

Reaction Steps

A mixture of 7-bromo-5-nitro-1H-indole (prepared according to the procedure set forth in L. L. Melhado et al., Phytochemistry, 21, 2879 (1982)) (550 mg, 2.28 mmol) in glacial acetic acid (16 mL) was treated with zinc dust (700 mg, 10.7 mmol) for 2 hours at room temperature. The mixture was then filtered through a pad of Celite, the filtrate evaporated, and coevaporated several times with toluene. The residue was taken up in methylene chloride (with a small amount of methanol), washed with saturated NaHCO3 solution, dried (Na2SO4), and evaporated. Flash chromatography eluting with 20% ethyl acetate in hexane afforded 153 mg of the title compound.

Provenance & Evidence