Ammonium Chloride → 1-[2-(Dimethylamino)ethyl]-1h-indazol-6-amine

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Reaction Steps

A mixture of dimethyl-[2-(6-nitro-indazol-1-yl)-ethyl]-amine (1 g, 4.3 mmol), iron powder (1.9 g, 34 mmol), and ammonium chloride (120 mg, 2.2 mmol) in a 4:1 Ethanol/H2O solution (20 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 10 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4), and the filtrate concentrated under reduced pressure to provide the title compound (0.8 g, 92%). 1H NMR (300 MHz, DMSO-d6) ppm 2.17 (s, 6H), 2.63(t, J=6.44, 2H), 4.23 (t, J=6.44, 2H), 5.28(s, 2H), 6.50 (m, 2H), 7.35 (m, 1H), 7.69 (m, 1H); MS (DCI/NH3) m/z 205 [M+H]+.

Provenance & Evidence