61494-42-6

17302-46-4

61494-42-6

GENERAL METHOD: Methyl 5-nitrosalicylate (0.79 g, 4 mmol) was dissolved in DMSO (8 mL) and mixed with a solution of hydroxylamine hydrochloride (0.60 g, 8.6 mmol) in water (2 mL). Subsequently, triethylamine (0.80 g, 8 mmol) was added to the mixture. The reaction mixture was stirred at 50 °C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and poured into water (30 mL) and filtered to remove unreacted methyl 5-nitrosalicylate. The filtrate was extracted with ethyl acetate (50 mL), the organic phase was washed sequentially with water (40 mL) and saturated brine (40 mL), and dried over anhydrous sodium sulfate. The organic solvent was removed by concentration under reduced pressure and the crude product was purified by washing with acetonitrile (3 mL) to give N,2-dihydroxy-5-nitrobenzamide in final 30% yield.