Potassium Cyanide → 2-(6-Chloropyridin-3-yl)acetonitrile

HRID 2245946Notes

Reaction equation

HRID 2245946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[C-:10]#[N:11].[K+]>C(O)C.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:10]#[N:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 14751282-(6-Chloropyridin-3-yl)acetonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (5.0 g, 0.031 mol) in ethanol (38 mL) and water (19 mL) was added potassium cyanide (2.41 g, 0.0370 mol) at RT under nitrogen atmosphere. The reaction mixture was stirred at 50° C. overnight. The reaction was diluted with water and extracted with DCM. The organic layer was washed with brine and dried over sodium sulfate. The solution was filtered and the filtrate was concentrated to afford the desired compound (4.2 g, 89%). Analytical LCMS: (M+H)+=153.1.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0522b78ead534bcd8f4171a947cbc2d5
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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