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

HRID 597767

Reaktionsgleichung

Reaktionsgleichung von HRID 597767
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.BrCCBr.[Mg].[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.[O:30]1CCCC1>CO>[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]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 8028Tetrahydrofuran2×HCID 3060571-IsoquinolinecarbonitrileHCID 5210591-Bromo-4-butylbenzeneHCID 5462224Magnesium

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Bromo-4-butylbenzene (2.29 ml, 13 mmol) and a catalytic amount of 1,2-dibromoethane as an initiator were added to a mixed solution of magnesium (338 mg, 14 mmol) and tetrahydrofuran (6.5 ml) under nitrogen atmosphere, and this mixture was stirred under reflux for 10 minutes. The mixture was cooled to 0° C., a solution of 1-isoquinolinecarbonitrile (1.0 g, 6.5 mmol) in tetrahydrofuran was added, and this mixture was stirred at room temperature for 1 hour, then at 70° C. for 3 hours. Thereafter, the mixture was cooled again to 0° C., concentrated hydrochloric acid (2.6 ml) and methanol (11 ml) were added, and this mixture was heated under reflux for 2 hours. After the mixture was concentrated, the residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was separated, washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.7 g).

Aufarbeitung

  1. temperatureunder reflux for 10 minutes
  2. stirringthis mixture was stirred at room temperature for 1 hour
  3. temperatureThereafter, the mixture was cooled again to 0° C.
  4. temperaturethis mixture was heated
  5. temperatureunder reflux for 2 hours
  6. concentrationAfter the mixture was concentrated
  7. dissolutionthe residue was dissolved in 5 N sodium hydroxide
  8. filtrationtoluene, and was filtered through celite
  9. customThe toluene layer of the filtrate was separated
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5eb775e0a146496484f22a1ce1040985
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897387B2

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