Ethyl bromoacetate → Ethyl 2-(2-oxopyridin-1-YL)acetate

HRID 1585173Notes

Reaction equation

HRID 1585173 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:13]([O:12][C:10]([CH2:9][N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 88712-PyridoneHCID 11430Potassium Carbonate

Product 1

HCID 9497629Ethyl 2-(2-oxopyridin-1-YL)acetateYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Pyridone (4.76 g, 50 mmol) and ethyl bromoacetate (10.02 g, 60 mmol) were dissolved in acetone (100 ml). Potassium carbonate (8.28 g, 60 mmol) was added to the solution and the mixture was refluxed for two hours with stirring. After being cooled, insoluble substances were removed by filtration and the filtrate was evaporated to dryness. The residue was purified by silica gel column chromatography, to thereby obtain N-ethoxycarbonylmethyl-2-pyridone (7.60 g, yield 84%).

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. temperatureAfter being cooled
  3. custominsoluble substances were removed by filtration
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f728c53f0d846a6a83b7a9e271341fd
Source dataset
uspto-grants-1999_08
Patent number
US05935977

Reaction notes

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