Acetic Anhydride → 4-Methoxypyridin-2(1H)-one

HRID 888101Notes

Reaction equation

HRID 888101 reaction equation
C(OC(=O)C)(=[O:3])C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=1>>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:3])[CH:11]=1

Participants

3

Conditions

Temperature
130 °C

Procedure

Acetic anhydride (36.3 mL) was added to 4-Methoxy pyridine N-oxide (1.09 g) and the resulting solution was warmed to 130° C. and stirred overnight. After 16 h of stirring, the crude mixture was concentrated on the rotavap. 10 mL of a 1:1 MeOH—H2O solution was added and the resulting mixture was stirred overnight. After 10 h, the mixture was concentrated to a solid. The solid was recrystallized in AcCN, filtered and rinsed with ether.

Workup

  1. stirringAfter 16 h of stirring
  2. concentrationthe crude mixture was concentrated on the rotavap
  3. addition10 mL of a 1:1 MeOH—H2O solution was added
  4. stirringthe resulting mixture was stirred overnight
  5. waitAfter 10 h
  6. concentrationthe mixture was concentrated to a solid
  7. customThe solid was recrystallized in AcCN
  8. filtrationfiltered
  9. washrinsed with ether

Sources & evidence

ORD record
ord-031d38de59d54ee5a19afd17f42927a3
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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