Water → 6-(8-Bromooctyloxy)-2-methoxyquinoline

HRID 68993

반응식

HRID 68993 반응식
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][CH3:15])[CH:8]=[CH:7]2.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.O>CN(C=O)C>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][CH3:15])[CH:8]=[CH:7]2

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783101,8-DibromooctaneHCID 45091192HCID 45091192, 화합물

생성물 1

HCID 669608866-(8-Bromooctyloxy)-2-methoxyquinoline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% in oil, 40 mg) was suspended in DMF (2 ml), and was cooled to 0° C. in ice water bath. 6-Hydroxy-2-methoxyquinoline (171 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. 1,8-Dibromooctane (0.37 ml) was added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1). The purified product was condensed to dryness under reduced pressure to give the title compound (225 mg) as a white powder.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customcondensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)
  6. customcondensed to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-0fe9cd0488094e2bb49d4aa4a48cdf44
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822453B2

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