Sodium Carbonate → 4-tert-butyl-2,3-dimethylpyridine N-oxide

HRID 35458Notes

Reaction equation

HRID 35458 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=1[CH3:12])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:21])C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][N+:8]([O-:21])=[C:7]([CH3:11])[C:6]=1[CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 21296013HCID 21296013, compound

Product 1

HCID 536584744-tert-butyl-2,3-dimethylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.5 g of 4-tert-butyl-2,3-dimethylpyridine in 120 ml of methylene chloride is treated at room temperature with 14.4 g of m-chloroperbenzoic acid. The reaction mixture is made basic with a saturated sodium carbonate solution and extracted. The organic solution is dried and concentrated. The residue is purified on a silica qel column, whereby the medium pressure flash chromatography method (solvent: methylene chloride/ethyl acetate, with increasing ethyl acetate concentrations) is used and the pressure is produced with nitrogen gas. The 4-tert-butyl-2,3-dimethylpyridine N-oxide obtained is processed directly.

Workup

  1. extractionextracted
  2. customThe organic solution is dried
  3. concentrationconcentrated
  4. customThe residue is purified on a silica qel column, whereby
  5. concentrationthe medium pressure flash chromatography method (solvent: methylene chloride/ethyl acetate, with increasing ethyl acetate concentrations)
  6. customthe pressure is produced with nitrogen gas

Sources & evidence

ORD record
ord-6c291d75f2e4481582b06b95df14ca72
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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