Synthesis
General procedure for the synthesis of 2-amino-3-methoxyphenol from 3-methoxy-2-nitrophenol: To a stirred solution of 3-methoxy-2-nitrophenol (8.78 g, 51.9 mmol) in ethanol (250 mL) was added 10% palladium-carbon catalyst (1 g), and the reaction mixture was stirred for 2.5 hr at room temperature and hydrogen atmosphere (1 atm). Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated in vacuum to afford 2-amino-3-methoxyphenol (7.09 g, 51.0 mmol, 98% yield) as a yellow solid. The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 3.85 (3H, s), 6.46 (1H, d, J = 7.9 Hz), 6.48 (1H, d, J = 7.9 Hz), 7.40 (1H, t, J = 7.9 Hz), 10.22 (1H, s).
References
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 5, p. 1644 - 1658
[2] Patent: EP2168959, 2010, A1. Location in patent: Page/Page column 123
