2,4-Dimethylpyridine → 2,4-Dimethylpyridine 1-oxide

HRID 640104

Reaction equation

HRID 640104 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][C:2]=1[CH3:8].ClC1C=C(C=CC=1)C(OO)=[O:14].S([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N+:1]=1[O-:14]

Participants

5

Reactant 3

HCID 79362,4-DimethylpyridineHCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 707332,4-Dimethylpyridine 1-oxideYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-lutidine (2.0 g, 18.7 mmol) in methylene chloride (100 mL) was added 3-chloroperoxybenzoic acid (5.07 g, 29.4 mmol), which was stirred for 20 minutes at room temperature. A small amount of saturated aqueous sodium hydrogen sulfite solution was added to the reaction solution, and the organic layer was separated after vigorous stirring. This organic layer was washed with 5 N aqueous sodium hydroxide solution (5.9 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure to obtain the title compound (1.54 g, 66.9%). The title compound was used in the following reaction without being purified.

Workup

  1. customthe organic layer was separated after vigorous stirring
  2. washThis organic layer was washed with 5 N aqueous sodium hydroxide solution (5.9 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-1b4146d5e3d94115ada3963dbb2d5206
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Linked notes

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