2-Chloro-4-methoxy-5-nitropyridine (208 mg, 1.10 mmol) was used as starting material, which was mixed with ammonium chloride (295 mg, 5.52 mmol) and iron powder (246 mg, 4.4 mmol) in a solvent mixture of ethanol (5 mL) and water (0.5 mL). The reaction mixture was heated and stirred at 80 °C for 18 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through a diatomaceous earth column and washed with methanol. The filtrate and washings were combined and the solvent was removed by concentration under reduced pressure. The residue was partitioned between dichloromethane (10 mL) and water (10 mL), the organic phase was separated and washed with water (10 mL). The aqueous phases were combined and back-extracted with dichloromethane (3 x 5 mL). All organic phases were combined, filtered through a hydrophobic membrane and concentrated under reduced pressure to remove the solvent to give the off-white solid product 6-chloro-4-methoxypyridin-3-amine (155 mg, 89% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.73 (s, 1H), 6.71 (s, 1H), 3.90 (s, 3H), 3.71 (s, 2H).
