Water → 2-[(6,7-Dimethoxy-4-quinolyl)oxy]naphthalene-1-carbaldehyde

HRID 228538

反応式

HRID 228538 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.[OH:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[CH:27]=[O:28].O>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:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[CH:27]=[O:28]

参加物

6

反応物 3

HCID 962WaterHCID 128192-Hydroxy-1-naphthaldehydeHCID 4596104-Chloro-6,7-dimethoxyquinoline

生成物 1

HCID 230784822-[(6,7-Dimethoxy-4-quinolyl)oxy]naphthalene-1-carbaldehyde収率 15%

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
160 °C

実験手順

4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-hydroxy-1-naphthoaldehyde (231 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (6 ml), and the suspension was stirred at 160° C. for 2 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and 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 using acetone-chloroform to give the title compound (24 mg, yield 15%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and 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

出典と根拠

ORDレコード
ord-3eda3425b3e0483e83bac2f7ede96c50
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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