Acetic Anhydride → 2-Acetoxymethyl-4-acetylaminopyridine

HRID 358577Notes

Reaction equation

HRID 358577 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N+:3]=1[O-].C([O-])([O-])=[O:11].[Na+].[Na+].[C:16]([O:19][C:20](=[O:22])[CH3:21])(=O)[CH3:17]>>[C:20]([O:19][CH2:16][C:17]1[CH:1]=[C:2]([NH:3][C:4](=[O:11])[CH3:5])[CH:7]=[CH:6][N:8]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 178428516HCID 178428516, compound

Product 1

HCID 199130032-Acetoxymethyl-4-acetylaminopyridine

Procedure

6.5 g of the thus obtained 2-methyl-4-aminopyridine-N-oxide were dissolved in 80 ml of acetic anhydride and heated for 3 hours at 80° to 100° C. The excess anhydride was decomposed with ice, the solution adjusted with Na2CO3 to pH 8 and extracted with dichloromethane. After rotating in the organic phase, 5 g of 2-acetoxymethyl-4-acetylaminopyridine were obtained.

Workup

  1. temperatureheated for 3 hours at 80° to 100° C
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-ff9e7a6232b0456fa2dc9fdc9ec28feb
Source dataset
uspto-grants-1991_03
Patent number
US04997835

Reaction notes

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