2,5-Dimethylpyridine → 2,5-Dimethylpyridin-1-ium-1-olate

HRID 2200597Notes

Reaction equation

HRID 2200597 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:17]

Participants

5

Reactant 3

HCID 115262,5-DimethylpyridineHCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium Hydroxide

Product 1

HCID 5717732,5-Dimethylpyridin-1-ium-1-olateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,5-dimethylpyridine (2.24 g, 21 mmol) in CHCl3(20 mL) was added MCPBA (4.31 g, 25 mmol) in portions over 30 min. The mixture was stirred at room temperature overnight. Calcium hydroxide (4 g, 54 mmol) was added to quench the reaction and the mixture was stirred vigorously for 3 h. The mixture was filtered through a Celite pad. The filtrate was concentrated and dried under vacuum to give 2,5-dimethylpyridine 1-oxide (2.5 g, 97.1% yield) as white solid, which was used without purification. CMS retention time 0.442 min; LCMS MH+ 124.

Workup

  1. customto quench
  2. customthe reaction
  3. stirringthe mixture was stirred vigorously for 3 h
  4. filtrationThe mixture was filtered through a Celite pad
  5. concentrationThe filtrate was concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-04000d43abfc4a32a1ebf43b5298ed87
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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