Hydrochloric Acid → (4-Butylphenyl)(isoquinolin-1-yl)methanone

HRID 597764

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HRID 597764 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Mg].BrCCBr.[C:17]1([C:27]#N)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][N:18]=1.Cl.[OH-:30].[Na+]>CO.O1CCCC1>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:27]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:30])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH3:11]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 3060571-IsoquinolinecarbonitrileHCID 5210591-Bromo-4-butylbenzeneHCID 5462224Magnesium

생성물 1

HCID 17851496(4-Butylphenyl)(isoquinolin-1-yl)methanone

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Under a nitrogen atmosphere, 1-bromo-4-butylbenzene (2.29 ml, 13.0 mmol) was added to a mixed solution of magnesium (338 mg, 13.9 mmol) and tetrahydrofuran (6.5 ml), and as an initiator, catalytic amount of 1,2-dibromoethane was added, and this was stirred under reflux for 10 minutes. The solution was cooled to 0° C., a tetrahydrofuran solution of 1-isoquinolinecarbonitrile (1.0 g, 6.49 mmol) was added, and was stirred for another 1 hour at room temperature, and at 70° C. for 3 hours. Subsequently, the solution was cooled again to 0° C., concentrated hydrochloric acid (2.56 ml) and methanol (11 ml) were added, and then refluxed for 2 hours. The concentrated residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was divided, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.72 g of the title compound.

후처리

  1. temperatureunder reflux for 10 minutes
  2. stirringwas stirred for another 1 hour at room temperature
  3. temperatureSubsequently, the solution was cooled again to 0° C.
  4. temperaturerefluxed for 2 hours
  5. filtrationtoluene, and was filtered through celite
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-75537fa6a5bc4eb78471a4412022a269
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897387B2

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