Dimethylformamide → 2-(2-Methoxypyridin-3-yl)acetonitrile

HRID 1837702Notes

Reaction equation

HRID 1837702 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]Cl)=[CH:7][CH:6]=[CH:5][N:4]=1.[C-]#N.[Na+].[CH3:14][N:15](C=O)C>O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:14]#[N:15])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 149329453-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 226785372-(2-Methoxypyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g of (2-methoxy-3-pyridyl)methyl chloride, 2.5 g of sodium cyanide and 10 ml of DMF were stirred under heating for 10 minutes. Water was added thereto, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The drying agent was removed, and the solvent was evaporated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1), to give 2.5 g of a colorless oil.

Workup

  1. temperatureunder heating for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f1231a14f7534ee4895c0a159a0db220
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

Loading…