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

HRID 1740968Notes

Reaction equation

HRID 1740968 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.OO.CC(C)=[O:18].C(OCC)(=O)C>C(O)(=O)C.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=1[O-:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 75812-(Phenylmethyl)pyridineHCID 21584569Ethylacetate acetone

Product 1

HCID 3155902-Benzyl-1-oxo-1lambda~5~-pyridineYield 79%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A stirred solution of 3.0 g (18 mmol) 2-benzylpyridine and 1.65 mL of 30% aqueous hydrogen peroxide in 5.0 mL of acetic acid was heated at 100° C. for 3 hr (S. Hibino and E. Sugino, J. Heterocycl Chem., 1990, 27, 175). After cooling to room temperature, the reaction was diluted with 30 mL ethyl acetate and neutralized with sodium carbonate. The sodium acetate was separated by filtration and the filtrate was dried (sodium carbonate) and concentrated to give a yellow oil. Flash column chromatography on 125 g of silica gel using 7 of L 20% acetone/ethyl acetate furnished 2,58 g (79% yield) of 2-benzylpyridine N-oxide as an amber syrup.

Workup

  1. customThe sodium acetate was separated by filtration
  2. dry with materialthe filtrate was dried (sodium carbonate)
  3. concentrationconcentrated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-4346749c5b2d49ccab28ff6f696e20a5
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

Loading…