3,4-Dimethylphenol → 6,7-Dimethoxy-4-(3,4-dimethylphenoxy)quinoline

HRID 228523

반응식

HRID 228523 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:18]=[C:19]([OH:24])[CH:20]=[CH:21][C:22]=1[CH3:23].[OH-].[Na+]>COCCOCCOC>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:24][C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:17]([CH3:16])[CH:18]=1

참가 물질

5

반응물 3

HCID 72493,4-DimethylphenolHCID 14798Sodium HydroxideHCID 4596104-Chloro-6,7-dimethoxyquinoline

생성물 1

HCID 230783876,7-Dimethoxy-4-(3,4-dimethylphenoxy)quinoline수율 58%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
180 °C

실험 절차

4-Chloro-6,7-dimethoxyquinoline (200 mg) and 3,4-dimethylphenol (274 mg) were suspended in diethylene glycol dimethyl ether (0.1 ml), and the suspension was stirred at 180° C. for 1.5 hr. The reaction solution was cooled to room temperature, an aqueous sodium hydroxide solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel using acetone-chloroform to give 6,7-dimethoxy-4-(3,4-dimethylphenoxy)quinoline (160 mg, yield 58%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-3d14fea65c3846f2920e7e82745b8e7b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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