Sodium Sulfite → 6-Methylpyridine-3-carbonitrile 1-oxide

HRID 639147Notes

Reaction equation

HRID 639147 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:15].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N+:3]=1[O-:15]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 2819956-Methylpyridine-3-carbonitrile

Product 1

HCID 198186716-Methylpyridine-3-carbonitrile 1-oxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6-Methylnicotinonitrile (3.68 g, 31.15 mmol) is dissolved in chloroform (60 ml). 3-Chloroperoxybenzoic acid (7.53 g, 32.71 mmol) is added dropwise as a solution in chloroform (60 ml), and the solution is stirred at room temperature overnight. Sodium sulphite (2.92 g, 23.17 mmol) is added, and the resulting mixture is stirred for one hour. The reaction is quenched with saturated sodium bicarbonate solution, and the product is extracted with chloroform (500 ml). The organic phase is washed with brine, dried over magnesium sulphate monohydrate, filtered and concentrated in vacuo. The residue is used without further purification.

Workup

  1. stirringthe resulting mixture is stirred for one hour
  2. customThe reaction is quenched with saturated sodium bicarbonate solution
  3. extractionthe product is extracted with chloroform (500 ml)
  4. washThe organic phase is washed with brine
  5. dry with materialdried over magnesium sulphate monohydrate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is used without further purification

Sources & evidence

ORD record
ord-469f1c21f9ae41348ba451526b59ca90
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

Loading…