Water → 6,7-Dimethoxy-4-[(1-methyl-5-indolyl)oxy]quinoline

HRID 228530노트

반응식

HRID 228530 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2.[H-].[Na+].[CH3:27]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:27])[CH:20]=[CH:19]2

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

생성물 1

HCID 231566486,7-Dimethoxy-4-[(1-methyl-5-indolyl)oxy]quinoline수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6,7-Dimethoxy-4-[(1H-5-indolyl)oxy]quinoline (50 mg) was dissolved in N,N-dimethylformamide (1 ml), and 60% sodium hydride (7 mg) was added, followed by stirring for 30 min under ice cooling. Methyl iodide (0.0107 ml) was added to the reaction solution, and the mixture was stirred under ice cooling for additional one hr. Water was 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 thin layer chromatography using methanol-chloroform to give the title compound (32 mg, yield 62%).

후처리

  1. stirringthe mixture was stirred under ice cooling for additional one hr
  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 thin layer chromatography

출처 및 근거

ORD 기록
ord-9122da5cd3ec4bf0beaa10e363c6457e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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