m-Chloroperbenzoic acid → 2-Chloro-4-methylpyridine 1-oxide

HRID 37852

Reaction equation

HRID 37852 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][N+:14]=1[O-:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 772482-Chloro-4-methylpyridine

Product 1

HCID 124874842-Chloro-4-methylpyridine 1-oxideYield 464.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

40% meta-chloroperbenzoic acid (13.5 g, 31.4 mmol) was added at ambient temperature to a solution of 2-chloro-4-methyl-pyridine (2.0 g, 1.5 mmol) in chloroform (20 mL) and heated at reflux for 24 h. After allowing to cool, the mixture was washed with water followed by sodium bicarbonate solution. The separated organic phase was further washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give a residue which was purified by column chromatography over silica gel (60-120 mesh) using 10% methanol in ethyl acetate as eluent to afford 2-chloro-4-methyl-pyridine 1-oxide (1.0 g, 45%) as a deep brown oily liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washthe mixture was washed with water
  5. washThe separated organic phase was further washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-c2ddec53bd744cd7b5a933c42f3d5d64
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

Loading…