Ammonium Chloride → HCID 22138917, compound

Participants

Reaction Steps

Dimethyl-[2-(5-nitro-indazol-2-yl)-ethyl]-amine (0.300 g, 1.28 mmol), iron powder (0.715 g, 12.8 mmol) and ammonium chloride (0.0343 g, 0.641 mmol) was suspended in a 4:1 ethanol/H2O solution. The mixture was heated to reflux for 3 hours, cooled to room temperature and the solvents were removed under vacuo. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes, filtered through a plug of silica gel followed by rinsing with triethylamine/ethyl acetate (1/4). The filtrate was concentrated to provide the titled product. 1H NMR (300 MHz, DMSO-d6) ppm 2.16 (s, 6H) 2.72 (t, 2H, J=6.44), 4.35 (t, 2H, J=6.44), 4.74 (s, 2H), 6.55 (dm, 1H), 6.72 (m, 1H), 7.30 (m, 1H), 7.89 (s, 1H); MS (DCI/NH3) m/z 205 [M+H]+.

Provenance & Evidence