Hydrogen Peroxide → 2,6-Dimethylpyridine N-oxide

HRID 1640952Notes

Reaction equation

HRID 1640952 reaction equation
[N:1]1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[OH:9]O>C(O)(=O)C>[N+:1]1([O-:9])[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 79372,6-Lutidine

Product 1

HCID 140832,6-Dimethylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2,6-lutidine (19, 23 ml, 200 mmol) and 50% hydrogen peroxide (15 ml) in glacial acetic acid (100 ml) is refluxed at 110° C. for 3 hours. The solution is then concentrated in vacuo at 40° C. to approximately 60 ml. Water (20 ml) is added, and the concentration process is repeated three times. The concentrated solution is further dried by lyophilizer overnight, yielding 26 g of 2,6-Lutidine 1-oxide (20) that contains approximately 10% acetic acid. 1H NMR (300 MHz, CDCl3) δ 2.52 (s, 6H), 7.15 (m, 3H). MS, m/z 124 (M+1), 247 (2M+1).

Workup

  1. concentrationThe solution is then concentrated in vacuo at 40° C. to approximately 60 ml
  2. additionWater (20 ml) is added
  3. customThe concentrated solution is further dried by lyophilizer overnight

Sources & evidence

ORD record
ord-74fafa1d8f2d421d9db878c7f39a5775
Source dataset
uspto-grants-2012_02
Patent number
US08114888B2

Reaction notes

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