2,4-Dimethylphenol → 4-(2,4-Dimethylphenoxy)-6,7-dimethoxyquinoline

HRID 228510

반응식

HRID 228510 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:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[OH:24].[OH-].[Na+]>COCCOCCOC>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[O:24][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

참가 물질

5

반응물 3

HCID 77712,4-DimethylphenolHCID 14798Sodium HydroxideHCID 4596104-Chloro-6,7-dimethoxyquinoline

생성물 1

HCID 230782534-(2,4-Dimethylphenoxy)-6,7-dimethoxyquinoline수율 46%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
180 °C

실험 절차

4-Chloro-6,7-dimethoxyquinoline (200 mg) and 2,4-dimethylphenol (0.267 ml) 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, and an aqueous sodium hydroxide solution was then added to the reaction solution. 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. The residue was purified by column chromatography on silica gel using acetone-chloroform to give 4-(2,4-dimethylphenoxy)-6,7-dimethoxyquinoline (127 mg, yield 46%).

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-5ada81207d734a66b4327bce86f025a4
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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