Sodium Cyanide → 2-(2-Chloropyridin-3-yl)acetonitrile

HRID 1692595Notes

Reaction equation

HRID 1692595 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]Cl)=[CH:6][CH:5]=[CH:4][N:3]=1.[C-:10]#[N:11].[Na+]>CS(C)=O>[Cl:1][C:2]1[C:7]([CH2:8][C:10]#[N:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 115283992-Chloro-3-chloromethyl-pyridine

Product 1

HCID 147395432-(2-Chloropyridin-3-yl)acetonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound (20.5 g) obtained in step 2 in DMSO (100 mL) was added sodium cyanide (12.4 g), and the mixture was stirred at 50° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was poured into a mixture of water and ethyl acetate. The organic layer was washed with brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane) to give (2-chloropyridin-3-yl)acetonitrile (11.7 g, 61%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was poured into a mixture of water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-416a54cf2fd64f5186e92abf04aada8f
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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