Pyridine → 4-Nitrophenyl hydrogen carbonimidate

Participants

Reaction Steps

To a stirred, cooled (about 0° C.) solution of methyl-3-amino-4-methoxy benzoate (5.0 g; 27.6 mmol) in dry dichloromethane (175 mL) was added pyridine (2.34 mL; 29 mmol) followed by 4-nitrophenyl chloroformate (5.8 9; 29 mmol) under a nitrogen (N2) atmosphere. After stirring for 8 hours, the, reaction was washed with 2N aqueous hydrochloric acid (2×200 mL), saturated aqueous sodium bicarbonate (2×200 mL), and brine (200 mL), then dried (MgSO4), and filtered. The filtered solution was diluted with ethyl acetate and hexanes (about 800 mL) until a precipitate formed. The solid was collected on a Buchner funnel with suction, and air dried to provide the desired carbamate as a white solid (70% yield).

Provenance & Evidence