2,3-Lutidine → Pyridine, 2,3-dimethyl-, 1-oxide

HRID 1720357Notes

Reaction equation

HRID 1720357 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:17])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:17]

Participants

5

Reactant 3

HCID 114202,3-LutidineHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium Hydroxide

Product 1

HCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To the 2,3-dimethylpyridine (15.0 g, 140 mmol) in CHCl3 (40 mL) at 0° C. was slowly added a CHCl3 (200 mL) solution of m-chloroperbenzoic acid (21.5 g, 154 mmol). The mixture was stirred 1 hour at 0° C., the ice bath was removed and stirring continued another hour. Calcium hydroxide (26 g, 350 mmol) was added and the slurry was vigorously stirred 4.5 hours before filtering through celite. The cake was thoroughly washed with CH2Cl2. Evaporation of the solvents left an oily solid that was swished in Et2O giving 8.71 g of desired product which was used without further purification.

Workup

  1. customthe ice bath was removed
  2. stirringstirring
  3. waitcontinued another hour
  4. waitthe slurry was vigorously stirred 4.5 hours
  5. filtrationbefore filtering through celite
  6. washThe cake was thoroughly washed with CH2Cl2
  7. customEvaporation of the solvents
  8. waitleft an oily solid
  9. customwas used without further purification

Sources & evidence

ORD record
ord-2ca50283559a47adb5f74c6e177e2cbe
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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