m-Chloroperbenzoic acid → 2-Cyano-4-methylpyridin-1-ium-1-olate

HRID 1476911Notes

Reaction equation

HRID 1476911 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)Cl>[C:8]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N+:5]=1[O-:18])#[N:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 887392-Cyano-4-methylpyridine

Product 1

HCID 37251652-Cyano-4-methylpyridin-1-ium-1-olateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methylpicolinonitrile (5 g, 42.3 mmol) in DCM (25 mL) was cooled in an ice/brine bath. To this solution was added mCPBA (14.61 g, 85 mmol). The reaction mixture was allowed to warm to RT and was stirred overnight. The mixture was subsequently diluted with DCM until all solids were dissolved and was washed with 1N NaOH (2×200 mL) and with brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a white solid (4.03 g, 71%). ESI-MS m/z [M+H]+ 135.1.

Workup

  1. dissolutionwere dissolved
  2. washwas washed with 1N NaOH (2×200 mL) and with brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe2150bbdeb44b7787b34db46176cd02
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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