Acetic Anhydride → 4-Benzyloxy-2(1H)-pyridone

HRID 15030

Reaction equation

HRID 15030 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=[O:18])C>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2958714-(Benzyloxy)pyridine N-oxide

Product 1

HCID 36077244-Benzyloxy-2(1H)-pyridoneYield 49%

Procedure

4-Benzyloxypyridine 1-oxide (24.8 g, 123 mmols) was refluxed in acetic anhydride (150 mL) for 1.5 hours. Cooling the system to room temperature, the system was concentrated under reduced pressure and the resulting residue was dissolved in a mixed solvent of ethyl acetate (150 mL) and methanol (10 mL), followed by stirring at 60° C. for 2 hours. The solid formed upon cooling the system to room temperature was recovered by filtration to provide crude title compound (8.84 g). Concentrating the filtrate, additional crude title compound (4.17 g) was obtained. The combined crude product was recrystallized from a mixed solvent of methanol and ethyl acetate to provide the title compound (12.1 g, 49%).

Workup

  1. concentrationthe system was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in a mixed solvent of ethyl acetate (150 mL) and methanol (10 mL)
  3. customThe solid formed
  4. temperatureupon cooling the system to room temperature
  5. filtrationwas recovered by filtration
  6. customto provide crude title compound (8.84 g)
  7. concentrationConcentrating the filtrate
  8. customadditional crude title compound (4.17 g) was obtained
  9. customwas recrystallized from a mixed solvent of methanol and ethyl acetate

Sources & evidence

ORD record
ord-49d140b0dab5425e960646c5242341e6
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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