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

HRID 228510

反応式

HRID 228510 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

反応条件

温度
180 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5ada81207d734a66b4327bce86f025a4
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

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