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

HRID 899964Notes

Reaction equation

HRID 899964 reaction equation
[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

Participants

6

Reactant 3

HCID 180AcetoneHCID 707665-AminoisoquinolineHCID 82115Trimethylsilyl cyanide

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

5.0 g (34.7 mmol) of 5-aminoisoquinolin, 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.

Workup

  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)

Sources & evidence

ORD record
ord-b1510ef9595d491480a34f0bf0656ebe
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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