Water → 2-(2-Methylpyridin-3-yl)acetonitrile

HRID 1975470Notes

Reaction equation

HRID 1975470 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[C-:10]#[N:11].[Na+].O.C(OCC)(=O)C>CS(C)=O>[C:10]([CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 122437113-(Chloromethyl)-2-methylpyridine

Product 1

HCID 190992862-(2-Methylpyridin-3-yl)acetonitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 3-chloromethyl-2-methylpyridine (9.2 g) and sodium cyanide (9.55 g) in dimethyl sulfoxide (80 ml) was stirred for 30 minutes at 80° C. The reaction mixture was poured into a mixture of water (200 ml) and ethyl acetate (1 l). Organic layer was separated, washed with brine and dried over magnesium sulfate. Concentration of the solvent gave a residue, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (1:4, V/V) to give 3-cyanomethyl-2-methylpyridine (7.6 g).

Workup

  1. customOrganic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customConcentration of the solvent gave a residue, which
  5. customwas chromatographed on silica gel (300 ml)
  6. washeluting with a mixture of hexane and ethyl acetate (1:4, V/V)

Sources & evidence

ORD record
ord-3e079fd07c8f4cf88dcd47c3657d7347
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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