Ammonium Chloride → HCID 22138910, compound

Participants

Reaction Steps

Dimethyl-[2-(5-nitro-indazol-2-yl)-ethyl]-amine (0.275 g, 1.17 mmol), iron powder (0.656 g, 11.7 mmol) and ammonium chloride (0.0314 g, 0.587 mmol) was suspended in a 4:1 ethanol/H2O solution. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed in vacuo and the residue stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes and then filtered through a plug of silica gel. After rinsing with triethylamine/ethyl acetate (1/4), the filtrate was concentrated to provide the title product. 1H NMR (300 MHz, DMSO-d6) ppm 2.16 (s, 6H), 2.71 (t, 2H, J=6.44), 4.31 (t, 2H, J=6.44), 4.98 (s, 2H), 6.46 (m, 1H), 6.50 (m, 1H), 7.33 (s, 1H), 8.03 (s, 1H); MS (DCI/NH3) m/z 205 [M+H]+.

Provenance & Evidence