Ethyl 5-nitro-1H-indole-2-carboxylate → Ethyl 5-amino-1H-indole-2-carboxylate

Participants

Reaction Steps

To a suspension of ethyl 5-nitro-1H-indole-2-carboxylate (0.100 g, 0.43 mmol) in 5 mL of absolute ethanol was added 5% palladium on carbon (0.045 g, 0.021 mmol). The mixture was evacuated and flushed with nitrogen, then filled with hydrogen at 50 psi. After 3 h, the reaction mixture was filtered through Celite and the filtrate was evaporated to give the title compound (0.053 g, 60%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.33 (s, 1H), 7.10 (d, 1H), 6.78 (d, 1H), 6.58-6.69 (m, 2H), 4.70 (br. s., 2H), 4.25 (q, 2H), 1.27 (t, 3H). MS: m/z 205 (M+1).

Provenance & Evidence