7-bromo-N,N-dipropylisoquinolin-1-amine → 1-(Dipropylamino)isoquinoline-7-carbonitrile

HRID 349050

Reaktionsgleichung

Reaktionsgleichung von HRID 349050
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[C:19]([Cu])#[N:20]>CN(C)C=O.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:19]#[N:20])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:14][CH3:15]

Komponenten

5

Edukt 2

HCID 210859987-bromo-N,N-dipropylisoquinolin-1-amineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 210851971-(Dipropylamino)isoquinoline-7-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-N,N-dipropylisoquinolin-1-amine (350 mg, 1.1 mmol) and CuCN (204 mg, 2.2 mmol) in N,N-dimethylformamide (2 mL) was stirred at reflux for 24 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate (3×50 mL). The combined organics were washed with saturated sodium chloride, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to provide 1-(dipropylamino)isoquinoline-7-carbonitrile (279 mg, which was used without any further characterization.

Aufarbeitung

  1. temperatureat reflux for 24 h
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with saturated sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-88b84d7a4f9244dda74bdc9b5db506a5
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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