7-Bromo-1-Chloroisoquinoline → 7-Bromo-1-butylisoquinoline

HRID 14265

반응식

HRID 14265 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[CH2:13]([Mg]Cl)[CH2:14][CH2:15][CH3:16]>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418265HCID 178418265, 화합물

생성물 1

HCID 210859957-Bromo-1-butylisoquinoline수율 24.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

To a refluxing solution of 7-bromo-1-chloroisoquinoline (4.85 g, 23.28 mmol) in diethyl ether (75 mL) was added butylmagnesium chloride (17.8 mL, 2.0 M ether, 35.6 mmol) and the reaction maintained at reflux for 2 h. The reaction mixture was cooled to room temperature, carefully diluted with an equal volume of ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an brown oil. Purification by flash column chromatography (silica, 1-10% ether/hexanes) gave the desired 7-bromo-1-butylisoquinoline (1.50 g): ESI MS m/z 264 [M+H]+.

후처리

  1. temperaturethe reaction maintained
  2. temperatureat reflux for 2 h
  3. washwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an brown oil
  8. customPurification by flash column chromatography (silica, 1-10% ether/hexanes)

출처 및 근거

ORD 기록
ord-a635181a8b834cb2a957fc968b143c5e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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