Ammonium Chloride → 5-Bromopyridine-2,3-diamine

Participants

Reaction Conditions

Reaction Steps

5-Bromo-3-nitropyridin-2-amine (3 g) was dissolved in isopropyl alcohol (56 mL) and water (28 mL). Ammonium chloride (1.47 g, 2 eq) was added followed by iron powder (2.31 g, 3 eq). The reaction was heated to 90° C. for 45 minutes. The solution was then cooled, and diluted with EtOAc, filtered, and the layers were separated. The organic layer was then washed with brine, dried over sodium sulfate, and concentrated delivering product as a solid (2.45 g, 95% yield). 1H-NMR (300 MHz, DMSO-d6) δ 7.25 (d, 1H), 6.77 (d, 1H), 5.70-5.40 (bs, 2H), 5.20-4.80 (bs, 2H).

Provenance & Evidence