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

HRID 6745

Reaction equation

HRID 6745 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 220184962-(5-Methoxy-4-methyl-1H-indol-3-yl)acetonitrileYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-72abe992e3ec45f2ad4431dc0d535d8d
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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