Methanol → 2-(1-Oxo-1lambda~5~-pyridin-2-yl)-1-phenylethan-1-one

HRID 974824Notes

Reaction equation

HRID 974824 reaction equation
[N+:1]1([O-:8])[C:2]([CH3:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[H-].[Na+].[C:11](OC)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>C1C=CC=CC=1.O>[O:18]=[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N+:1]=1[O-:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 7150Methyl BenzoateHCID 136022-Methylpyridine 1-oxideHCID 24758Sodium hydride

Product 1

HCID 3494282-(1-Oxo-1lambda~5~-pyridin-2-yl)-1-phenylethan-1-oneYield 82.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2-picoline N-oxide (4.4 g, 0.04 mol) in benzene (25 ml) was added to a suspension of sodium hydride (3.2 g of 60% oil dispersion) and methyl benzoate (9.94 ml, 0.08 mol) in dry benzene (100 ml). The reaction mixture was refluxed overnight. Methanol (15 ml) was added to the cooled reaction mixture, followed by water (150 ml). The aqueous layer was separated and extracted with chloroform (2×40 ml). The aqueous layer was acidified with 1N HCl and extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated to give the subtitle ketone as a solid (7 g), mp 146°-148° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe aqueous layer was separated
  3. extractionextracted with chloroform (2×40 ml)
  4. extractionextracted with chloroform
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8170cedf9ef4776acc694d2363530c4
Source dataset
uspto-grants-1997_03
Patent number
US05607935

Reaction notes

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