(4-Nitrophenyl)acetic acid → N-Methoxy-N-methyl-2-(4-nitrophenyl)acetamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of (4-nitrophenyl)acetic acid (30.0 g), N,O-dimethylhydroxylamine hydrochloride (21.0 g) and 1-hydroxybenzotriazole monohydrate (33.0 g) in DMF (450 ml) were added triethylamine (30 ml) and 4-(N,N-dimethylamino)pyridine (130 mg), and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (41.4 g) was added to the mixture, and then, the mixture was stirred overnight under nitrogen atmosphere. Water was added to the mixture, and the mixture extracted with ethyl acetate twice. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate once, with water twice, and with saturated brine once, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid was washed with hexane to give N-methoxy-N-methyl-2-(4-nitrophenyl)acetoamide (32.6 g) as colorless crystals.

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