Hydrogen Peroxide → 2-tert-Butyl-1-oxo-1lambda~5~-pyridinato

HRID 1171470Notes

Reaction equation

HRID 1171470 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:11]O>CC(O)=O.C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N+:6]=1[O-:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 1386302-(t-Butyl)-pyridine

Product 1

HCID 187150642-tert-Butyl-1-oxo-1lambda~5~-pyridinatoYield 71.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-tert-Butylpyridine (2.00 g, 14.8 mmol, 1 eq.) was dissolved in HOAc (10 mL) and 30% hydrogen peroxide (1.68 mL, 14.8 mmol, 1 eq.) at room temperature then the reaction was refluxed for 20 hours. The reaction was stripped to obtain an amber oil which was dissolved in methylene chloride (10 mL) then dried over sodium sulfate and stripped to obtain 2-tert-butylpyridine-N-oxide (1.60 g) as an amber oil. Yield=71.5%. LCMS detects (M+H)+=152.09.

Workup

  1. customto obtain an amber oil which
  2. dry with materialthen dried over sodium sulfate

Sources & evidence

ORD record
ord-1c1295db44b94ab1905e4e7a81a7d94f
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

Loading…