m-Chloroperbenzoic acid → 2-Chloromethyl-3-methylpyridine 1-oxide

HRID 703152Notes

Reaction equation

HRID 703152 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 130586822-(Chloromethyl)-3-methylpyridine

Product 1

HCID 221514452-Chloromethyl-3-methylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 24 g of 2-chloromethyl-3-methylpyridine in 200 ml of methylene chloride was treated while cooling with ice with a solution of 44 g of m-chloroperbenzoic acid in 200 ml of methylene chloride. The reaction mixture was heated under reflux for 2 hours and concentrated in a rotary evaporator. The residue was chromatographed on silica gel with ethyl acetate/methylene chloride (3:1) as the elution agent, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. The 2-chloromethyl-3-methyl-pyridine 1-oxide obtained was processed directly.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated in a rotary evaporator
  4. customThe residue was chromatographed on silica gel with ethyl acetate/methylene chloride (3:1) as the elution agent
  5. customthe pressure being produced with nitrogen gas

Sources & evidence

ORD record
ord-b46db194000e4d4c89b10e855c94073f
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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