2,6-Lutidine → 2,6-Dimethylpyridine N-oxide

HRID 1860387Notes

Reaction equation

HRID 1860387 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].ClC1C=CC=C(C(OO)=[O:16])C=1.[N:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:26]>C(Cl)Cl>[N+:19]1([O-:16])[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:26]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 140832,6-Dimethylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium sulphate (6 g) and a solution of m-chloroperbenzoic acid (40 g) in DCM (140 ml) was added to a solution of 2,6-lutidine (5 ml) in dry DCM (60 ml). The mixture was stirred at 23° and under a nitrogen atmosphere for 18 h; then it was quenched with a saturated aqueous sodium bicarbonate solution (200 ml). Then a solution of potassium carbonate was added and the aqueous phase was saturated with NaCl and then it was extract with DCM (3×100 ml). The organic extract was dried and concentrated in vacuo to a yellow oil which was purified by flash chromatography (eluting in gradient from EA to EA-MeOH 9:1) to give the title compound as a yellow oil (4.7 g).

Workup

  1. customthen it was quenched with a saturated aqueous sodium bicarbonate solution (200 ml)
  2. additionThen a solution of potassium carbonate was added
  3. extractionit was extract with DCM (3×100 ml)
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated in vacuo to a yellow oil which
  7. customwas purified by flash chromatography (eluting in gradient from EA to EA-MeOH 9:1)

Sources & evidence

ORD record
ord-e21c929b0d0547f09663b0a11b70155e
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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