Ammonium Chloride → 3-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-one

Participants

Reaction Steps

A mixture of 3-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-one (200 mg, 0.72 mmol), iron powder (400 mg, 7.1 mmol), and ammonium chloride (20 mg, 0.37 mmol) in a 4:1 ethanol/H2O solution (5 mL) was heated to reflux for 3 hours, cooled to room temperature, concentrated under reduced pressure. The resudue 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). The filtrate was concentrated under reduced pressure to provide the title compound (120 mg, 67%). 1H NMR (300 MHz, DMSO-d6) ppm 4.03 (s, 3H), 4.42 (d, J=6.10, 1H), 6.04 (m, 1H), 7.25 (m, 1H), 7.32 (m, 1H), 7.38 (m, 1H), 7.48 (m, 2H), 7.69 (m, 1H), 7.79 (m, 1H), 8.44 (m, 1H), 9.12 (s, 1H); MS (DCI/NH3) m/z 247 [M+H]+.

Provenance & Evidence