Synthesis
Step 2: Pd/C (10%) was added to a solution of N-methyl-2,4-dinitroaniline (12.14 g, 60.9 mmol) in acetonitrile (35 mL) and triethylamine (36.4 mL). The reaction mixture was cooled to -15 °C, followed by dropwise addition of formic acid (11.1 mL) to a solution of acetonitrile (35 mL). The reaction mixture was refluxed for 3 hours and then thermally filtered. The filtrate was concentrated under reduced pressure to afford N1-methyl-4-nitrobenzene-1,2-diamine (Product 2) as a red liquid in >95% yield.
References
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 16, p. 2567 - 2571
[2] Patent: WO2010/85377, 2010, A2. Location in patent: Page/Page column 41
[3] Journal of the Indian Chemical Society, 1988, vol. 65, # 8, p. 567 - 570
[4] Patent: EP2769723, 2014, A1. Location in patent: Paragraph 0160-0161
[5] Patent: WO2014/128206, 2014, A1. Location in patent: Page/Page column 51
