Potassium Cyanide → 2-(5-Methoxy-4-methyl-1H-indol-3-yl)acetonitrile

HRID 6745

Reaktionsgleichung

Reaktionsgleichung von HRID 6745
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15]N(C)C>O.CN(C)C=O>[CH3:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:1]#[N:2]

Komponenten

5

Edukt 2

HCID 9032Potassium CyanideHCID 22018474(5-methoxy-4-methyl-1H-indol-3-ylmethyl)dimethylamine

Produkt 1

HCID 220184962-(5-Methoxy-4-methyl-1H-indol-3-yl)acetonitrileAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of potassium cyanide (0.74 g) in 20 mL water was added a solution of (5-methoxy-4-methyl-1H-indol-3-ylmethyl)dimethylamine (0.5 g) in 20 mL of N,N-dimethylformamide. The solution was heated to reflux for 40 min, cooled to rt, and 40 mL of ice water was added. The aqueous layer was extracted with three portions of toluene, and the combined toluene layers were washed with water and brine. The solvent was removed in vacuo and the product purified by column chromatography dichloromethane) as the mobile phase to yield (5-methoxy-4-methyl-1H-indol-3-yl)-acetonitrile (0.40 g).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 40 min
  3. extractionThe aqueous layer was extracted with three portions of toluene
  4. washthe combined toluene layers were washed with water and brine
  5. customThe solvent was removed in vacuo
  6. customthe product purified by column chromatography dichloromethane) as the mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-72abe992e3ec45f2ad4431dc0d535d8d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084154B2

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