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

HRID 703150Notes

Reaction equation

HRID 703150 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>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:17]

Participants

4

Reactant 2

HCID 114202,3-LutidineHCID 70297m-Chloroperbenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 24 g of 2,3-d1methylpyridine in 100 ml of methylene chloride was treated while cooling with ice with a solution of 46.6 g of m-chloroperbenzoic acid in 100 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 ohloride (3:1) as the elution agent. the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. By recrystallization from ether there was obtained 2,3-dimethylpyridine 1-oxide of melting point 56°.

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 ohloride (3:1) as the elution agent
  5. customthe pressure being produced with nitrogen gas
  6. customBy recrystallization from ether

Sources & evidence

ORD record
ord-a342b0915e8940ec9022d3328d63b115
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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