Water → 1-(Pyridin-4-yl)cyclopropanecarbonitrile

HRID 966419Notes

Reaction equation

HRID 966419 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.[NH2-].[Na+].Br[CH2:13][CH2:14]Br.O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:8]#[N:9])[CH2:14][CH2:13]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24533Sodium amideHCID 41120852-(Pyridin-4-yl)acetonitrile

Product 1

HCID 223148081-(Pyridin-4-yl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.5 g of 4-pyridylacetonitrile are added to a mixture of 2.5 g of sodium amide in 80 ml of DCM, followed by 2.6 ml of 1,2-dibromoethane, and the mixture is stirred overnight at RT. The reaction-mixture is poured into water and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvents are evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with DCM and then with a DCM/MeOH mixture from (99/1; v/v) to (95/5; v/v). 2.5 g of the expected product are obtained.

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase is washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvents are evaporated off under vacuum
  5. customThe residue is chromatographed on silica gel
  6. washeluting with DCM

Sources & evidence

ORD record
ord-7f22b9c8be4a4c9891ceef759ee9fe39
Source dataset
uspto-grants-2005_10
Patent number
US06951940B2

Reaction notes

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