Cyclohexanone → 2-Chloro-6-methylpyridine 1-oxide

HRID 1975743Notes

Reaction equation

HRID 1975743 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.C1(=[O:15])CCCCC1.OOS([O-])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+]>O.C1COCC1>[Cl:1][C:2]1[N+:7]([O-:15])=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 876016-Chloro-2-picolineHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 45797722-Chloro-6-methylpyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-2-methylpyridine (49.04 g; 384 mmol) in 500 mL pH 8 buffer and 300 mL THF was added cyclohexanone (3.77 g; 38.4 mmol) and Oxone® (potassium peroxymonosulfate) (236.3 g; 384 mmol). After stirring for three days an additional portion of Oxone® (236.3 g; 384 mmol) was added and the reaction was stirred for 24 hours. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated. The 6-chloro-2-methylpyridine-N-oxide was used with no further purification.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe 6-chloro-2-methylpyridine-N-oxide was used with no further purification

Sources & evidence

ORD record
ord-da3ebdd549c74032b96b22652ce3a1ac
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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