General procedure for the synthesis of 2-amino-5-methoxypyridine from 2-bromo-3-methoxy-6-nitropyridine: 2-bromo-3-methoxy-6-nitropyridine (1.20 g, 5.15 mmol), hydrazine hydrate (6 mL), Pd/C (10%, 400 mg), and ethanol (40 mL) were mixed and heated to reflux for 45 minutes. Upon completion of the reaction, the mixture was allowed to cool and filtered through Celite. The filtrate was concentrated, water (20 mL) and saturated ammonia (10 mL) were added and extracted with chloroform (2 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give 2-amino-5-methoxypyridine as a colorless solid with a low melting point. Yield: 615 mg (96%).1H NMR (DMSO-d6, 400MHz) δ 7.64 (dd, 1H), 7.10 (dd, 1H), 6.42 (dd, 1H), 5.43 (br.s, 2H), 3.68 (s, 3H).
