Benzyl Alcohol → 3-benzyloxycarbonylamino-6-methyl-2-pyridinone

Participants

Reaction Steps

DPPA (8.5 mL, 39.2 mmol) was added to a stirred mixture of 2-hydroxy-6-methylpyridine-3-carboxylic acid (6.00 g, 39.2 mmol) and triethylamine (5.5 mL, 39.2 mmol) in anhydrous dioxane (72 mL) and the resulting solution was refluxed for 16 hours. Triethylamine (5.5 mL, 39.2 mmol) and benzyl alcohol (4.2 mL, 36.8 mmol) were added and the solution was refluxed for further 24 hours. The reaction mixture was concentrated in vacuo. To the residue were added dichloromethane (130 mL) and saturated NaCl solution and the mixture was acidified with 1M HCl to pH=1 (43 mL). The water phase was extracted with dichloromethane twice; the combined organic phases were washed with saturated NaHCO3 solution, saturated NaCl solution and dried (Na2SO4). The solvent was evaporated under reduced pressure and the product was recrystallized from methanol to give 4.95 g (19,2 mmol) of the solid brown compound.

Provenance & Evidence