Water → 4-[(1,6-Dibromo-2-naphthyl)oxy]-6,7-dimethoxyquinoline

HRID 228527

反応式

HRID 228527 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.[Br:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[OH:28].O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Br:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[O:28][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

6

反応物 3

HCID 962WaterHCID 277682-Naphthol, 1,6-dibromo-HCID 4596104-Chloro-6,7-dimethoxyquinoline

生成物 1

HCID 688297184-[(1,6-Dibromo-2-naphthyl)oxy]-6,7-dimethoxyquinoline収率 67%

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
150 °C

実験手順

4-Chloro-6,7-dimethoxyquinoline (223 mg), 1,6-dibromo-2-naphthol (910 mg), and 4-dimethylaminopyridine (366 mg) were suspended in o-dichlorobenzene (3 ml), and the suspension was stirred at 150° C. for 4 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 4-[(1,6-dibromo-2-naphthyl)oxy]-6,7-dimethoxyquinoline (326 mg, yield 67%).

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-1c329b09909a4651a0afb3a40c21d47c
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

読み込み中…