Acetyl chloride → N-Acetyl-N-(3-methoxyphenyl)hydroxylamine

Participants

Reaction Steps

Under ice-cooling, 10% palladium on activated carbon (0.46 g) and hydrazine monohydrate (4.9 mL, 100 mmol) were added to a solution of 3-nitroanisole (7.7 g, 50 mmol) in tetrahydrofuran-ethanol solution (1:1, 100 mL), stirred for 3 hours at room temperature, and let stand overnight at about 5° C. The whole was filtered with celite with ethanol (100 mL), and the filtrate was concentrated under reduced pressure. Sodium hydrogen carbonate (13 g, 150 mmol) and anhydrous N,N-dimethylformamide (50 mL) were added to the obtained residue. Moreover under ice-cooling, acetyl chloride (5.4 mL, 76 mmol) was added thereto and the mixture was stirred for 1 hour. The reaction solution was diluted with water (200 mL) and extracted with ethyl acetate (300 mL×1, 200 mL×1). The combined organic layer was washed with brine (100 mL×2) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatograpy to give the title reference compound (9.3 g) as an orange oil (quantitative yield)

Provenance & Evidence