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

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.

1. temperaturethe resulting solution was refluxed for 16 hours
2. temperaturethe solution was refluxed for further 24 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionTo the residue were added dichloromethane (130 mL) and saturated NaCl solution
5. extractionThe water phase was extracted with dichloromethane twice
6. washthe combined organic phases were washed with saturated NaHCO3 solution, saturated NaCl solution
7. dry with materialdried (Na2SO4)
8. customThe solvent was evaporated under reduced pressure
9. customthe product was recrystallized from methanol

ORD record

ord-aeab8a7244dc4e459d6805767fb1c631

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524871B2