Water → (4-Methylpyridin-2-yl)acetonitrile

HRID 1419854Notes

Reaction equation

HRID 1419854 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1.[C-:10]#[N:11].[K+].O>CS(C)=O>[C:10]([CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)#[N:11]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 126752612-(Chloromethyl)-4-methylpyridine

Product 1

HCID 12812206(4-Methylpyridin-2-yl)acetonitrileYield 1,112.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-chloromethyl-4-methylpyridine (3.70 g, 2.17 mmol) was dissolved in dimethyl sulfoxide (9 ml) and herein potassium cyanide (1.70 g, 2.60 mmol) was added. After stirring for 17 hours at room temperature, water was added and it was extracted twice with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to get crude product. The residue was separated and purified by column-chromatography over silica gel to obtain the desired product (3.19 g, yield=95%).

Workup

  1. extractionit was extracted twice with diethyl ether
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto get crude product
  5. customThe residue was separated
  6. custompurified by column-chromatography over silica gel

Sources & evidence

ORD record
ord-7cb8e14c17ad495b86580b80c13e8021
Source dataset
uspto-grants-1999_03
Patent number
US05889027

Reaction notes

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