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

HRID 1374244Notes

Reaction equation

HRID 1374244 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

Preparation C3, Step 1: 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-51fc4c6ac0ba46bd9f7bff9ec20eb53f
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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