2-(Tert-butyl)-6-nitro-1H-indole → 2-(tert-Butyl)-1H-indol-6-amine

Participants

Reaction Steps

To a solution of 2-tert-butyl-6-nitro-1H-indole (1.3 g, 6.0 mmol) in MeOH (10 mL) was added Raney Ni (0.2 g). The mixture was stirred at room temperature under H2 (1 atm) for 3 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was washed with petroleum ether to give 2-tert-butyl-1H-indol-6-ylamine (B-6) (1.0 g, 89%). 1H NMR (DMSO-d6) δ 10.19 (s, 1 H), 6.99 (d,J=8.1 Hz, 1 H), 6.46 (s, 1 H), 6.25 (dd,J=1.8, 8.1 Hz, 1 H), 5.79 (d,J=1.8 Hz, 1 H), 4.52 (s, 2 H), 1.24 (s, 9 H); ESI-MS 189.1 m/z (MH+).

Provenance & Evidence