Ethyl 7-nitro-1H-indole-2-carboxylate → 1H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

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Reaction Steps

Platinum(IV) oxide (0.024 g, 0.107 mmol) was added to a suspension of ethyl 7-nitro-1H-indole-2-carboxylate (0.10 g, 0.30 mmol) in ethanol (20 mL) in a Fisher-Porter vessel. The mixture was evacuated and flushed with nitrogen three times, flushed with hydrogen (60 psi) and evacuated three times, then filled with hydrogen (60 psi). After 30 min, the reaction mixture was filtered through celite. The filtrate was concentrated and the residue was purified by column chromatography (hexane/EtOAc) to give the title compound (0.324 g, 74%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 9.60 (s, 1H), 7.22 (d, 1H), 7.19 (d, 1H), 6.94-7.03 (m, 1H), 6.66 (d, 1H), 4.43 (q, 2H), 1.44 (t, 3H). MS: m/z 205 (M+1).

Provenance & Evidence