Synthesis
General procedure for the synthesis of methyl 2-amino-6-methylbenzoate from methyl 2-methyl-6-nitrobenzoate: Methyl 2-methyl-6-nitrobenzoate (3.80 g, 19.5 mmol) was mixed with 10% palladium-carbon catalyst (1.03 g in 50% water) in methanol (20 mL) and the reaction was stirred for 1.5 h at 20-25 °C under hydrogen atmosphere. Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration, followed by distillation under reduced pressure to remove the solvent to afford the target product methyl 2-amino-6-methylbenzoate (3.13 g, 97% yield). The product was characterized by 1H-NMR (CDCl3) with chemical shifts δ: 2.43 (3H, s), 3.88 (3H, s), 6.52 (1H, d, J=7.9 Hz), 6.54 (1H, d, J=7.9 Hz), 7.08 (1H, t, J=7.9 Hz).
References
[1] Chemical Communications, 2005, # 44, p. 5583 - 5585
[2] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5956 - 5968
[3] Patent: EP1844768, 2007, A1. Location in patent: Page/Page column 27
[4] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[5] Patent: US2002/19414, 2002, A1
