Synthesis
General procedure for the synthesis of 3-methoxy-5-(trifluoromethyl)aniline from 3-nitro-5-(trifluoromethyl)anisole: 1-methoxy-3-nitro-5-(trifluoromethyl)benzene (8.50 g, 38.4 mmol) and 10% Pd/C catalyst (2.00 g, 1.88 mmol) were placed in methanol (40 mL), and the reaction was stirred at room temperature in a hydrogen atmosphere. The reaction was carried out for 24 hours. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to afford the title compound 3-methoxy-5-trifluoromethylaniline (7.2 g) as an orange solid. The product was analyzed by LC-MS (ESI): m/z [M+H]+ calculated value, retention time 1.56 min.
References
[1] Synthesis, 2006, # 19, p. 3316 - 3340
[2] Patent: US2005/54850, 2005, A1
[3] Journal of the Chemical Society, 1951, p. 2013,2016
[4] Journal of the American Chemical Society, 1955, vol. 77, p. 2284,2285
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1977, p. 14 - 17
