Acetic Anhydride → HCID 59311490, compound

HRID 1693333Notes

Reaction equation

HRID 1693333 reaction equation
[CH2:1]([C:3]1[C:8]([CH3:9])=[CH:7][N+:6]([O-])=[C:5]([CH3:11])[C:4]=1[CH3:12])[CH3:2].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][CH2:11][C:5]1[C:4]([CH3:12])=[C:3]([CH2:1][CH3:2])[C:8]([CH3:9])=[CH:7][N:6]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 672799884-Ethyl-2,3,5-trimethyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 59311490HCID 59311490, compoundYield 76%

Procedure

A mixture composed of the above 4-ethyl-2,3,5-trimethylpyridine 1-oxide (3.84 g) and acetic anhydride (50 mL) was heated under reflux for 30 minutes. After leaving to cool to room temperature, the reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform and then washed with a saturated sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (3.64 g, 76%) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customAfter leaving
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with a saturated sodium bicarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-196edf87bcb145518cbf6988aff65fb9
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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