Hydrogen Peroxide → HCID 67272106, compound

HRID 250951Notes

Reaction equation

HRID 250951 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:11])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].[OH:12]O>CC(O)=O>[CH2:1]([C:5]1[C:6]([CH3:11])=[N+:7]([O-:12])[CH:8]=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 13780551HCID 13780551, compound

Product 1

HCID 67272106HCID 67272106, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

3-Isobutyl-2-methyl-pyridine (Ishiguro et al. Yakugaku Zasshi 1958, 78, 220) (970 mg, 6.51 mmol) was suspended in a mixture of hydrogen peroxide (5 mL) and HOAc (45 mL) and the resulting mixture was stirred at 100° C. for 2.5 hours. The solvent was removed under reduced pressure and the resulting oily mixture was quenched with saturated NaHCO3 (60 mL) and extracted with CH2Cl2 (10×100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to yield 3-isobutyl-2-methyl-pyridine-1-oxide as a colorless oil (821 mg, 76%). 1H NMR (CDCl3) δ 0.93 (d, 6H, J=6.0 Hz), 1.84 (m, 1H), 2.51 (d, 2H, J=6.0 Hz), 2.52 (s, 3H), 7.03 (m, 2H), 8.18 (d, 1H, J=6.0 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting oily mixture was quenched with saturated NaHCO3 (60 mL)
  3. extractionextracted with CH2Cl2 (10×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93a222dcf1d44dd79103a30de2a59f40
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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