Potassium Cyanide → 2-Methoxy-6-quinolinecarbonitrile

HRID 986015노트

반응식

HRID 986015 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 201589792-Methoxy-6-quinolinecarbonitrile

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d8223615ddfd4c29b1ff007e6b02f216
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04710507

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