Acetic Acid → 4-Benzyl-1-oxo-1lambda~5~-pyridine

HRID 1861778Notes

Reaction equation

HRID 1861778 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:16])C.OO>C([O-])(O)=O.[Na+]>[CH2:1]([C:8]1[CH:13]=[CH:12][N+:11]([O-:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 164584-Benzylpyridine

Product 1

HCID 3155894-Benzyl-1-oxo-1lambda~5~-pyridineYield 98%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-benzylpyridine (5 mL, 30 mmol), acetic acid (30 mL) and 30% hydrogen peroxide (10 mL) was heated at 80-90° C. for 5 h. Concentration under reduced pressure gave an oil that was diluted with NaHCO3 (100 mL) and extracted with CH2Cl2 (2×100 mL). The collected organic phase was washed with brine (100 mL) and evaporated in vacuo to give the title compound as a colorless oil (5.68 g, 98%): 1H NMR (DMSO-d6) δ3.90 (s, 2H), 7.15-7.35 (m, 7H), 8.08 (d, J=6.3 Hz, 2H).

Workup

  1. concentrationConcentration under reduced pressure
  2. customgave an oil that
  3. extractionextracted with CH2Cl2 (2×100 mL)
  4. washThe collected organic phase was washed with brine (100 mL)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e13ade55bbc9452a8c642a3dd9c1252b
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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