General procedure for the synthesis of methyl (2-nitrophenyl)acetate from o-nitrophenylacetic acid:
(A) Preparation of methyl 2-(2-nitrophenyl)acetate
2-(2-Nitrophenyl)acetic acid (5.06 g, 27.9 mmol) was dissolved in methanol (100 mL) and concentrated sulfuric acid (5 mL) was added slowly and dropwise. The reaction mixture was heated under reflux conditions for 16 hours. Upon completion of the reaction, the solvent was removed by evaporation and water was added to the residue, which was subsequently extracted with ethyl acetate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave the title compound as a light orange oil (5.37 g, 99.0% yield).
1H-NMR (CDCl3) δ: 3.72 (3H, s), 4.03 (2H, s), 7.36 (1H, d, J = 7.3 Hz), 7.44-7.51 (1H, m), 7.57-7.63 (1H, m), 8.12 (1H, d, J = 7.8 Hz).
