3-Benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 5-(benzyloxy)-2-methylpyridin-4(1H)-one

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Reaction Conditions

Reaction Steps

A mixture of 3-benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (5.2 g, 20.0 mmol) in dimethylformamide (12 mL) was heated in an oil bath for 8 h. The temperature of the oil bath was maintained at 120° C. A solid separated upon cooling to RT. The solid 5-benzyloxy-2-methyl-1H-pyridin-4-one was suction filtered and washed with hexane. The isolated solid was dried under high vacuum for 16 h (3.32 g, 77% yield). 1H NMR (400 MHz, MeOH-D4) δ (ppm): 7.45-7.46 (m, overlapping peaks, 2H, Ar—H and CH), 7.29-7.39 (m, overlapping peaks, 4H, Ar—H), 6.34 (s, 1H, CH), 5.07 (s, 2H, OCH2), 2.30 (s, 3H, CH3); MS-ESI (m/z): 216.3 [M+1]+, 215.6 [M]+, 188.3.

Provenance & Evidence