Potassium Cyanide → 2-Methoxy-6-quinolinecarbonitrile

HRID 986015ノート

反応式

HRID 986015 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 201589792-Methoxy-6-quinolinecarbonitrile

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d8223615ddfd4c29b1ff007e6b02f216
出典データセット
uspto-grants-1987_12
特許番号
US04710507

反応ノート

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