m-Chloroperbenzoic acid → 2-Cyano-3-methylpyridine 1-oxide

HRID 1799551Notes

Reaction equation

HRID 1799551 reaction equation
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:18])[C:3]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 450798222-Cyano-3-methylpyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methylpyridine-2-carbonitrile (10 g, 85 mmol) was taken up in DCM (180 mL) and mCPBA (20.9 g, 93 mmol) was added. The resulting mixture was stirred at room temperature overnight. Additional mcpba (9.49 g, 42 mmol) was added and stirring continued at room temperature for 24 hours. Saturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×), followed by 20% MeOH—CHCl3 (2×). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-20% MeOH/EtOAc) gave the title compound as a white solid.

Workup

  1. additionAdditional mcpba (9.49 g, 42 mmol) was added
  2. stirringstirring
  3. waitcontinued at room temperature for 24 hours
  4. extractionSaturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by silica gel chromatography (0-20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-735702f7157143a9901ec02472c14caa
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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