Potassium Carbonate → HCID 68702328, compound

HRID 1437346Notes

Reaction equation

HRID 1437346 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[CH3:21][O:20][C:18]([CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1)=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 904066-Methyl-1-oxo-1lambda~5~-pyridin-3-ol

Product 1

HCID 68702328HCID 68702328, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the pyridine N-oxide (a) (21.12 g) in DMF (450 ml) was treated with potassium carbonate (26.2 g) then, after 30 minutes, with methyl bromoacetate (16 ml), and stirred overnight. Solvent was evaporated, saturated brine (500 ml) added and the mixture extracted with chloroform (6×200 ml). The combined organic solution was dried and evaporated and the residue chromatographed (20% EtOH in EtOAc) to give a solid (18.5 g).

Workup

  1. customSolvent was evaporated
  2. additionsaturated brine (500 ml) added
  3. extractionthe mixture extracted with chloroform (6×200 ml)
  4. customThe combined organic solution was dried
  5. customevaporated
  6. customthe residue chromatographed (20% EtOH in EtOAc)

Sources & evidence

ORD record
ord-fadcd898787446378e078f9db020b134
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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