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4-Chloro-6,7-dimethoxyquinoline → Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-6-methylbenzoate

HRID 228625
ノート
印刷プレビュー

反応式

HRID 228625 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:18]=[CH:19][CH:20]=[C:21]([OH:28])[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]>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:28][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:16])[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 584222Ethyl 2-hydroxy-6-methylbenzoate

生成物 1

HCID 57756350Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-6-methylbenzoate収率 91.3%

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
120 °C

実験手順

4-Chloro-6,7-dimethoxyquinoline (112 mg), ethyl 6-methylsalicylate (360 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight and was further stirred at 140° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then 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 (168 mg, yield 91%).

後処理

  1. stirringwas further stirred at 140° C. for 2 hr
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was removed by distillation under the reduced pressure
  4. additionWater was then 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-9845176dbbe1460683bc8cdfa08873e6
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07560558B2

反応ノート

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