Ammonia → HCID 86721347, compound

Participants

Reaction Steps

[step 1] 2-Methoxy-6-nitroaniline (4.0 g, 23.8 mmol) was dissolved in DMA (24 mL), pyridine (5.8 mL, 71.4 mmol) and 2-methoxyacetyl chloride (6.5 mL, 71.4 mmol) were added at 0° C., and the mixture was stirred at room temperature for 1 hr. Under ice-cooling, methanol and aqueous ammonia solution were added to the mixture, and the mixture was stirred at room temperature for 30 min. Water was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-30/70 v/v) to give 2-methoxy-N-(2-methoxy-6-nitrophenyl)acetamide (5.4 g, 95%).

Provenance & Evidence