Ammonium Chloride → 3-Amino-5-bromo-2-chloropyridine

Participants

Reaction Steps

To a solution of 5-bromo-2-chloro-3-nitropyridine (10.0 g, 42.1 mmol) in EtOH (70 ml) and H2O (14 ml) was added iron (11.7 g, 211 mmol) and NH4Cl (6.76 g, 126 mmol) at room temperature. The mixture was refluxed for 1 hour, and then cooled to room temperature, filtered through a Celite pad and washed with EtOH. The filtrate was concentrated in vacuo. The residue was treated with saturated aq. NaHCO3, and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (Hexane:EtOAc=3:1) to give 5-bromo-2-chloropyridin-3-amine (7.93 g, 91%) as a white solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 5.89 (2H, s), 7.30 (1H, d, J=2.0 Hz), 7.66 (1H, d, J=2.4 Hz).

Provenance & Evidence