5-Nitroindazole → 1H-Indazol-5-amine

Participants

Reaction Steps

A mixture of 5-nitro-1H-indazole (25 g, 0.153 mmol, commercially available) and 10% Pd/C (2.0 g) in MeOH was stirred under H2 (1 atm) overnight. After filtration, the filtrate was concentrated to yield 20 g (97%) of 1H-indazol-5-amine as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 12.50 (brs, 1H), 7.70 (s, 1H), 7.21 (d, J=8.7 Hz, 1H), 6.77 (d, J=8.7 Hz, 1H), 6.74 (s, 1H), 4.71 (brs, 1H), 3.15 (d, J=4.8 Hz, 2H); MS (ESI) m/z: 134 (M+H+).

Provenance & Evidence