Synthesis
3-Nitroaniline (1.2 g, 8.7 mmol) was dissolved in anhydrous dichloromethane (50 mL) and triethylamine (6 mL, 43.0 mmol) was added. Propionyl chloride (1.5 mL, 17 mmol) was slowly added dropwise under ice bath conditions, and stirring was continued in the ice bath after the drop was completed. Subsequently, the reaction mixture was allowed to slowly warm up to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction mixture was diluted with water (150 mL) and then extracted with dichloromethane (150 mL x 3). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate, v/v=3/1) to afford 1.6 g of the light yellow solid product N-(3-nitrophenyl)propionamide in 95% yield.
