Hydrogen Peroxide → Pyridine, 3-(phenylmethyl)-, 1-oxide

HRID 2396758Notes

Reaction equation

HRID 2396758 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=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:9]=[N+:10]([O-:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 121123-Benzylpyridine

Product 1

HCID 54142008Pyridine, 3-(phenylmethyl)-, 1-oxideYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-benzylpyridine (25 g, 0.148 tool) in hydrogen peroxide (30%, 15.1 mL) and acetic acid (100 mL) was refluxed for one day. Then more hydrogen peroxide (3 mL) was added and the resulting mixture was refluxed overnight. The reaction mixture was then evaporated and partitioned between a mixture of 3 N HCl, brine and dichloromethane. The organic layer was separated, dried and evaporated to give the desired compound (27.6 g, 100%).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customThe reaction mixture was then evaporated
  3. custompartitioned between a mixture of 3 N HCl, brine and dichloromethane
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-3e12e8445c50462ea540c0fda3bb7416
Source dataset
uspto-grants-1996_02
Patent number
US05494919

Reaction notes

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