2-Propenylphenol → 6,7-Dimethoxy-4-[2-(1-propenyl)phenoxy]quinoline

HRID 228507

反応式

HRID 228507 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.[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])=[CH:17][CH3:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[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:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH:16]=[CH:17][CH3:18]

参加物

5

反応物 2

HCID 930292-PropenylphenolHCID 4596104-Chloro-6,7-dimethoxyquinoline

生成物 1

HCID 688300666,7-Dimethoxy-4-[2-(1-propenyl)phenoxy]quinoline収率 43%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
140 °C

実験手順

4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-(1-propenyl)phenol (231 μl), and 4-dimethylaminopyridine (220 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Thereafter, water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water 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 using acetone-hexane to give the title compound (137 mg, yield 43%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed
  3. distillationby distillation under the reduced pressure
  4. additionThereafter, water was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed
  9. distillationby distillation under the reduced pressure
  10. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-a52adc89b48246fda8d251cbb92b06a7
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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