Water → Methyl 3-[(6,7-dimethoxy-4-quinolyl)oxy]naphthalene-2-carboxylate

HRID 228603

반응식

HRID 228603 반응식
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[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1.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[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]2[C:19]([CH:18]=1)=[CH:20][CH:21]=[CH:22][CH:23]=2

참가 물질

6

반응물 3

HCID 962WaterHCID 70163Methyl 3-hydroxy-2-naphthoateHCID 4596104-Chloro-6,7-dimethoxyquinoline

생성물 1

HCID 23156523Methyl 3-[(6,7-dimethoxy-4-quinolyl)oxy]naphthalene-2-carboxylate수율 4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
150 °C

실험 절차

4-Chloro-6,7-dimethoxyquinoline (100 mg), methyl 2-hydroxy-3-naphthoate (271 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (6 ml), and the suspension was stirred at 150° 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 (7 mg, yield 4%).

후처리

  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

출처 및 근거

ORD 기록
ord-e71ebc302da742f38cfca225e11c4dbb
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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