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

HRID 1455342Notes

Reaction equation

HRID 1455342 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-e2b770de86f04b09beee93a9f9b05bbc
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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