Dimethyl Sulfate → 4-Methoxy-N-methyl-3-nitrobenzeneacetamide

Participants

Reaction Steps

To a solution of 4.2 g (19.8 mmol) of 4-hydroxy-N-methyl-3 -nitrobenzeneacetamide in 50 mL of DMF containing 5.5 g of anhydrous potassium carbonate was added 5.6 mL of dimethyl sulfate. The mixture was heated at 60°-70° C. for 45 min, treated with an additional 3.0 mL of methyl sulfate, and heated for another 30 min. The mixture was cooled, poured into 200 mL water, and extracted with dichloromethane. The extracts were washed with water, dried and evaporated to give a solid which was recrystallized from ethanol-water to afford 3.7 g of a yellowish solid (82%). 1H NMR (300 MHz, CDCl3) δ 7.71 (s, 1H), 7.47 (d, 1H, J =9.0 Hz), 7.25 (d, 1H, J =8.4 Hz), 5.71 (brs, 1H), 3.90 (s, 3H) 3.47 (s, 2H), 2.75 (d, 3H, J=4.8 Hz).

Provenance & Evidence