Potassium Cyanide → 2-Methoxy-6-quinolinecarbonitrile

HRID 986015Notes

Reaction equation

HRID 986015 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2.[C-:14]#[N:15].[K+].[OH-].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2)#[N:15]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 14797Potassium HydroxideHCID 106575386-Bromo-2-methoxyquinoline

Product 1

HCID 201589792-Methoxy-6-quinolinecarbonitrile

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-2-methoxyquinoline (0.476 g), potassium cyanide (0.26 g), potassium hydroxide (0.05 mg) and palladium (II) acetate (0.067 g) in DMF (2.0 cm3) were heated at 135° for 3 hours. The cooled solution was then partitioned between water (20 cm3) and chloroform (50 cm3) and the aqueous phase was further extracted with chloroform (2×25 cm3). The combined and dried (MgSO4) extracts were evaporated in vacuo and the residue was chromatographed on silica (Merck "MK 60.9385") eluting with toluene to afford, after collection and evaporation of appropriate fractions, 6-cyano-2-methoxyquinoline, m.p. 163°-165°, (0.216 g).

Workup

  1. temperaturewere heated at 135° for 3 hours
  2. customThe cooled solution was then partitioned between water (20 cm3) and chloroform (50 cm3)
  3. extractionthe aqueous phase was further extracted with chloroform (2×25 cm3)
  4. dry with materialdried (MgSO4) extracts
  5. customwere evaporated in vacuo
  6. customthe residue was chromatographed on silica (Merck "MK 60.9385")
  7. washeluting with toluene
  8. customto afford
  9. customafter collection and evaporation of appropriate fractions, 6-cyano-2-methoxyquinoline, m.p. 163°-165°, (0.216 g)

Sources & evidence

ORD record
ord-d8223615ddfd4c29b1ff007e6b02f216
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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