Water → 1-(Pyridin-4-yl)cyclopropane-1-carbonitrile

HRID 478593

Reaction equation

HRID 478593 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)cyclopropane-1-carbonitrile

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-23620d53f18047f994f82ec60f6e2889
Source dataset
uspto-grants-2003_11
Patent number
US06642233B1

Linked notes

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