Hydrogen Peroxide → 2-Benzyl-1-oxo-1lambda~5~-pyridine

HRID 2081577Notes

Reaction equation

HRID 2081577 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14]O>C(O)(=O)C>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=1[O-:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 75812-(Phenylmethyl)pyridine

Product 1

HCID 3155902-Benzyl-1-oxo-1lambda~5~-pyridineYield 99.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-benzylpyridine (10.0 g, 0.059 moles) and hydrogen peroxide (33% w/v, 4.02 g, 12.2 ml, 0.118 moles) in glacial acetic acid (40 ml) was heated at 60° C. for 17 hours. The reaction mixture was cooled to room temperature, the acetic acid evaporated under reduced pressure and the residue dissolved in chloroform. After neutralisation with potassium carbonate (20 g) the chloroform was removed to give 2-benzylpyridine-N-oxide (10.86 g, 99%) as a viscous oil which crystallised on standing.

Workup

  1. customthe acetic acid evaporated under reduced pressure
  2. dissolutionthe residue dissolved in chloroform
  3. customAfter neutralisation with potassium carbonate (20 g) the chloroform was removed

Sources & evidence

ORD record
ord-2fc156addcf546b79a1475884229092c
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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