Synthesis
General procedure for the synthesis of 2-iodo-5-methoxyaniline from 4-iodo-3-nitroanisole: To a 100 mL methanol solution of 4-iodo-3-nitroanisole (5 g, 17.9 mmol) was added FeCl3 (50 mg, 0.3 mmol) and activated carbon (40 mg). The mixture was heated to reflux and hydrazine hydrate (1.75 g, 35 mmol) was added slowly and dropwise. After keeping the reaction at reflux for 8 h, it was cooled to room temperature and the reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated and purified by column chromatography (eluent: hexane solution of 10% ethyl acetate) to afford 4.05 g of the target product 2-iodo-5-methoxyaniline as a light yellow oil (91% yield).1H NMR (300 MHz, CDCl3) δ 7.47 (1H, d, J = 8.7 Hz), 6.31 (1H, d, J = 2.8 Hz), 6.13 (1H, d, J = 2.8 Hz) 6.13 (1H, dd, J = 2.8, 8.7 Hz), 3.73 (3H, s).
References
[1] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7354 - 7358
[2] Journal of Organic Chemistry, 2001, vol. 66, # 13, p. 4525 - 4542
[3] Patent: WO2003/106462, 2003, A1. Location in patent: Page 110
[4] Tetrahedron Letters, 2008, vol. 49, # 2, p. 363 - 366
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 48, p. 9262 - 9265
