Phenylacetonitrile → 2-Amino-3-phenylpropanenitrile
Reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[C-:20]#[N:21].C([Al+]CC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[NH2:9][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:20]#[N:21]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
10 millimoles (1.17 g) of benzyl cyanide are dissolved in 10 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of 1.5 M toluenic solution of diisobutylaluminum hydride (10 ml) are added, dropwise, at this temperature. The temperature is maintained at 0° C. for one hour, then 13.7 ml (viz 1.5 eq) of diethyl-aluminum cyanide are added. The reaction mixture is stirred for 3 hours while the temperature reaches the room temperature. Then it is hydrolyzed with 10 ml of methanol, and with a slurry of sodium sulfate. After purification of the so-obtained α-aminonitrile, by ethyl acetate/petroleum ether, there are obtained 0.95 g of 2-amino-3-phenyl-propionitrile, in the form of an orange-colored oil, yield: 65%.
Workup
- customthe room temperature
- customAfter purification of the so-obtained α-aminonitrile
Sources & evidence
- ORD record
- ord-fd09d88d817046619c32cfcd0082b793
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04942221
Reaction notes
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