Synthesis
General procedure: tert-butyl (3-nitrophenyl)carbamate (10.75 g, 45.12 mmol) was used as raw material and dissolved in methanol (150 mL). To this solution, 10% Pd/C catalyst (0.48 g) was added. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (4:1, v/v) to give N-BOC-mesophenylenediamine as a light yellow solid (7.59 g, 8% yield).
References
[1] Tetrahedron Letters, 1993, vol. 34, # 49, p. 7823 - 7826
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 623 - 639
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2253 - 2261
[4] Journal of the American Chemical Society, 2008, vol. 130, # 45, p. 15193 - 15202
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 212 - 221
