Acetic Anhydride → 4-Methoxypyridin-2(1H)-one
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]=1Participants
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
- stirringAfter 16 h of stirring
- concentrationthe crude mixture was concentrated on the rotavap
- addition10 mL of a 1:1 MeOH—H2O solution was added
- stirringthe resulting mixture was stirred overnight
- waitAfter 10 h
- concentrationthe mixture was concentrated to a solid
- customThe solid was recrystallized in AcCN
- filtrationfiltered
- washrinsed with ether
Sources & evidence
- ORD record
- ord-031d38de59d54ee5a19afd17f42927a3
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247556B2
Reaction notes
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