Benzonitrile → 2-Amino-2-phenylacetonitrile

HRID 2165894Notes

Reaction equation

HRID 2165894 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C[Si]([C:23]#[N:24])(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[NH2:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:23]#[N:24]

Participants

7

Reactant 4

HCID 7505BenzonitrileHCID 24436Sodium SulfateHCID 82115Trimethylsilyl cyanideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 408382-Amino-2-phenylacetonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

10 millimoles (1.031 g) of benzonitrile are dissolved in 10 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (10 ml) are added dropwise, at this temperature. The reaction mixture is maintained at 0° C. for 1 hour, then 2 ml (1.5 eq) of trimethylsilyl cyanide are added. The stirring is maintained for 3 hours at room temperature, then the mixture is hydrolyzed with 10 ml of methanol, then with pasty sodium sulfate. After purification of α-aminonitrile by an acid-base extraction there are obtained 0.820 g of 2-amino-2-phenyl-acetonitrile, with a yield of 62%.

Workup

  1. temperatureThe stirring is maintained for 3 hours at room temperature
  2. customAfter purification of α-aminonitrile
  3. extractionby an acid-base extraction

Sources & evidence

ORD record
ord-13b5c50a3b724a20955c648c6ddd4c14
Source dataset
uspto-grants-1990_07
Patent number
US04942221

Reaction notes

Loading…