4-Bromo-2,6-dimethylquinoline → 4-Cyano-2,6-dimethylquinoline

HRID 1581453Notes

Reaction equation

HRID 1581453 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[C:14]([Cu])#[N:15]>CN(C=O)C>[C:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)#[N:15]

Participants

4

Reactant 2

HCID 149913604-Bromo-2,6-dimethylquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 149913674-Cyano-2,6-dimethylquinolineYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 4-bromo-2,6-dimethylquinoline (5.0 g) and CuCN (4.82 g) were added to DMF (70 ml) and were allowed to react for 6 hours at a temperature of 140° C. Ice was poured to the reaction solution and the produced precipitate was removed through filtering. The filtrate was extracted using ethyl acetate, the solvent was removed under reduced pressure, and the residue was purified through column chromatography (silica gel, hexane/ethyl acetate=4/1) to obtain 4-cyano-2,6-dimethylquinoline (2.14 g) represented by the following chemical formula (47).

Workup

  1. customto react for 6 hours at a temperature of 140° C
  2. additionIce was poured to the reaction solution
  3. customthe produced precipitate was removed
  4. filtrationthrough filtering
  5. extractionThe filtrate was extracted
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified through column chromatography (silica gel, hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-ace30e94cb794f45b8109612a8052ec2
Source dataset
uspto-grants-2004_05
Patent number
US06730418B2

Reaction notes

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