Acetone → 2-(Isoquinolin-5-ylamino)-2-methylpropionitrile

HRID 1169659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1169659
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[CH3:12][C:13]([CH3:15])=O.C[Si]([C:20]#[N:21])(C)C>C(#N)C.[Cl-].[Zn+2].[Cl-]>[CH:7]1[C:8]2[C:3](=[C:2]([NH:1][C:13]([CH3:15])([CH3:12])[C:20]#[N:21])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 707665-AminoisoquinolineHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 684491322-(Isoquinolin-5-ylamino)-2-methylpropionitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5.0 g (34.7 mmol) of 5-aminoisoquinoline, 5.1 ml (69.4 mmol) of acetone and 945 mg (6.94 mmol) of zinc chloride were dissolved in 100 ml of acetonitrile and treated at 0° C. with 6.9 g (69.4 mmol) of trimethylsilyl cyanide. The mixture was refluxed for 3 hours, the solvent was then evaporated off and the residue was taken up in 200 ml of sodium hydrogen carbonate and extracted three times with ethyl acetate. The combined organic phases were dried and the residue remaining after evaporation was purified by flash chromatography (SiO2, methylene chloride/methanol=95/5) to give 6.0 g (82%) of the desired product.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hours
  2. customthe solvent was then evaporated off
  3. extractionextracted three times with ethyl acetate
  4. customThe combined organic phases were dried
  5. customafter evaporation
  6. customwas purified by flash chromatography (SiO2, methylene chloride/methanol=95/5)

Quellen und Nachweise

ORD-Eintrag
ord-c1f47604cd2648b7b9472349476e0c37
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825115B2

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