Water → 4-[2-(4-Fluoro-phenyl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline

HRID 228848노트

반응식

HRID 228848 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([OH:18])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([O:18][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 190675902-(4-Fluorophenyl)-quinolin-3-ol

생성물 1

HCID 577564954-[2-(4-Fluoro-phenyl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline수율 64%

시약·촉매·용매 2

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

반응 조건

온도
145 °C

실험 절차

2-(4-Fluoro-phenyl)-quinolin-3-ol (52 mg), 4-chloro-6,7-dimethoxyquinoline (145 mg), and 4-dimethylaminopyridine (214 mg) were suspended in o-dichlorobenzene (6 ml), and the suspension was stirred at 145° C. for 5 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 organic layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (59 mg, yield 64%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-3e480cd1cfa54bb790f0967de092a19a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

반응 노트

불러오는 중…