3-(tert-Butyl)-6-nitro-1h-indole → 3-(tert-Butyl)-1h-indol-6-amine

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Reaction Steps

A suspension of 3-tert-butyl-6-nitro-1H-indole (3.0 g, 14 mmol) and Raney Nickel (0.5 g) was hydrogenated under H2(1 atm) at room temperature for 3 h. The catalyst was filtered off and the filtrate was concentrated to dryness. The residue was purified by column on silica gel (petroleum ether/ethyl acetate=4:1) to give 3-tert-butyl-1 H-indol-6-amine (2.0 g, 77%) as a gray solid. 1 H NMR (CDCl3) δ 7.58(m, 2H), 6.73(d, J=1.2 Hz, 1H), 6.66(s, 1H), 6.57(dd, J=0.8, 8.6 Hz, 1H), 3.60(br, 2H), 1.42(s, 9H).

Provenance & Evidence