Synthesis
Step 1) Synthesis of methyl 2-methyl-6-nitrobenzoate (2): 2-methyl-6-nitrobenzoic acid (1; 10 g, 55.2 mmol) was dissolved in 200 mL of methyl ethyl ketone, iodomethane (17.2 mL, 276.0 mmol) and anhydrous potassium carbonate (38.1 g, 276.0 mmol) were added. The reaction mixture was stirred under reflux conditions for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (300 mL), washed sequentially with water (2 x 50 mL) and saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 10.80 g of methyl 2-methyl-6-nitrobenzoate (2). Mass spectrometry (ESI) analysis: the calculated value of C9H9NO4 was 195.05 and the measured value was 196 [M + H].
References
[1] Chemical Communications, 2005, # 44, p. 5583 - 5585
[2] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5956 - 5968
[3] Patent: US2011/251395, 2011, A1. Location in patent: Page/Page column 15
[4] Patent: US2005/49253, 2005, A1. Location in patent: Page/Page column 25-26
[5] Patent: US2005/54670, 2005, A1. Location in patent: Page/Page column 27
