Potassium Iodide → 7-(Pyridin-3-YL)heptanenitrile

HRID 1583421Notes

Reaction equation

HRID 1583421 reaction equation
[C-:1]#[N:2].[K+].[I-].[K+].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Cl)[CH:7]=1>CN(C)C=O.O>[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:1]#[N:2])[CH:7]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 135575283-(6-Chlorohexyl)pyridine

Product 1

HCID 137397387-(Pyridin-3-YL)heptanenitrileYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.0 g of potassium cyanide, 0.85 g of potassium iodide and 10.1 g of 6-(3-pyridyl)hexyl chloride in 100 ml of dimethylformamide was heated at 100° C. overnight. The reaction mixture was diluted with 200 ml of water and was extracted with dichloromethane. The combined organic layers were washed with water, dried over potassium carbonate and were evaporated. The residue was distilled to give 8.1 g (84%) of 3-pyridine heptanenitrile.

Workup

  1. extractionwas extracted with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over potassium carbonate
  4. customwere evaporated
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c3aa296857b643fd97ce27678c121ce5
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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