Ammonium Chloride → 1h-Indazol-4-amine,3-chloro-1-[2-(1-pyrrolidinyl)ethyl]-

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Reaction Steps

A mixture of 3-Chloro-4-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.40 g, 1.4 mmol), iron powder (0.76 g, 14 mmol), and ammonium chloride (37 mg, 0.68 mmol) in 80% Ethanol 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, 20 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4), and concentrated to provide the title compound (0.30 g, 84%). 1H NMR (300 MHz, DMSO-d6) ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.81 (t, 2H, J=6.78), 4.31 (t, 2H, J=6.78), 5.62 (s, 2H), 6.23 (d, 1H, J=7.46), 6.73 (d, 1H, J=8.48), 7.09 (m, 1H); MS (DCI/NH3) m/z 265 [M+H]+.

Provenance & Evidence