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

Participants

Reaction Steps

To a solution of 5-bromo-2-chloro-3-nitropyridine (4.24 g, 17.86 mmol) in EtOH (89 ml) was added Tin(II) chloride (16.9 g, 89.0 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 EtOAc. The filtrate was concentrated in vacuo. The residue was treated with saturated aq. NaHCO3, and extracted with EtOAc. The combined organic layers were washed brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1) to give 5-bromo-2-chloropyridin-3-amine (2.7 g, 73%) as a white solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 5.89 (2H, brs), 7.30 (1H, d, J=2.0 Hz), 7.66 (1H, d, J=2.4 Hz).

Provenance & Evidence