Synthesis
The general procedure for the synthesis of methyl 4-amino-3-methylbenzoate from methyl 3-methyl-4-nitrobenzoate was as follows: methyl 3-methyl-4-nitrobenzoate (50 g, 256.2 mmol) was dissolved in methanol (1.5 L), and palladium carbon catalyst (2.5 g) was added. Hydrogen (H2) was passed into the reaction mixture at room temperature and the reaction was continuously stirred overnight. Upon completion of the reaction, the solid catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford the light yellow solid product methyl 4-amino-3-methylbenzoate (38 g, 90% yield). The product was analyzed by LCMS (electrospray ionization, positive ion mode) with a mass-to-charge ratio (m/z) of 166.1, corresponding to the [M + H]+ ion peak.
References
[1] Tetrahedron, 2018, vol. 74, # 47, p. 6795 - 6803
[2] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4582 - 4589
[4] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
[5] Zeitschrift fur Anorganische und Allgemeine Chemie, 2014, vol. 640, # 1, p. 159 - 167
