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

HRID 1099046Notes

Reaction equation

HRID 1099046 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-8b8967fc86f6455f84797d500948425f
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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