Pyridine → HCID 18447399, compound

Participants

Reaction Steps

To a solution of 2-methoxy-1-(methoxymethoxy)-4-nitrobenzene (1.2 g, 5.63 mmol) in ethyl acetate (30 ml) was added 10%-Pd/C (120 mg) at room temperature, and reaction was carried out under a hydrogen atmosphere. After 30 minutes, the mixture thus obtained was filtered by the use of Celite and the filtrate was concentrated under reduced pressure. To a solution of the resulting residue in ethyl acetate (30 ml) were added pyridine (0.546 ml, 6.75 mmol) and pivaloyl chloride (0.763 ml, 6.19 mmol) at 0° C., and the resulting mixture was warmed up to room temperature. After 15 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution and the resulting mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain N-[3-methoxy-4-(methoxymethoxy)phenyl]-2,2-dimethylpropanamide (1.48 g, 98%).

Provenance & Evidence