2-Bromo-6-chloro-4-methylpyridine → 6-Chloro-4-methylpyridine-2-carbonitrile

HRID 725753Notes

Reaction equation

HRID 725753 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[Cu](C#N)[C:11]#[N:12]>CN(C)C=O>[Cl:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:11]#[N:12])[N:3]=1

Participants

4

Reactant 2

HCID 111172342-Bromo-6-chloro-4-methylpyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 230023726-Chloro-4-methylpyridine-2-carbonitrileYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20.7 g of 2-bromo-6-chloro-4-methylpyridine in 100 ml anhydrous N,N-dimethylformamide 9.9 g of copper cyanide was added. The reaction mixture was heated to reflux for 7 hours. After cooling, the mixture was filtered through a silica gel column with 500 ml ethyl acetate. The obtained solution was washed with a saturated aqueous solution of sodium chloride. The solvent was removed in vacuo and the residue purified by silica gel column chromatography using hexane/ethyl acetate. 1:1. 7.6 g (54%) of the title compound was obtained as a white solid of melting point 133° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through a silica gel column with 500 ml ethyl acetate
  5. washThe obtained solution was washed with a saturated aqueous solution of sodium chloride
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f195e96df4442e6b63b24ff03283627
Source dataset
uspto-grants-1998_01
Patent number
US05707933

Reaction notes

Loading…