m-Chloroperbenzoic acid → 6-Methylpyridine-3-carbonitrile 1-oxide

HRID 358983

Reaction equation

HRID 358983 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>ClCCl>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[N+:3]([O-:18])[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2819956-Methylpyridine-3-carbonitrile

Product 1

HCID 198186716-Methylpyridine-3-carbonitrile 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-methylnicotinonitrile (4.15 g) and 3-chloroperbenzoic acid (8.3 g) in dichloromethane (200 ml) was stirred under an argon atomosphere at room temperature for 16h. The dichloromethane was evaporated under reduced pressure and the residue purified by flash column chromatography on silica (K60), using ethyl acetate and then methanol: dichloromethane (1:9 by volume) as eluting solvent to give 5-cyano-2-methylpyridine-1-oxide, mp 133.5°.

Workup

  1. customThe dichloromethane was evaporated under reduced pressure
  2. customthe residue purified by flash column chromatography on silica (K60)
  3. washmethanol: dichloromethane (1:9 by volume) as eluting solvent

Sources & evidence

ORD record
ord-a78378da87434bf7a8573388e582ea7e
Source dataset
uspto-grants-1991_03
Patent number
US04999364

Linked notes

Loading…