Benzonitrile → 2-Amino-2-phenylacetonitrile

HRID 1029812Notes

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-:19]#[N:20].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CN(C)C=O.CO>[NH2:8][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:19]#[N:20]

Participants

Conditions

Temperature: 0 °C

Procedure

20 millimoles (2.06 g) of benzonitrile are dissolved in 20 ml of anhydrous toluene, at 0° C., under an argon atmosphere. 30 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (20 ml) are added, dropwise, at this temperature. The temperature is maintained at 0° C. for 1 hour, then the reaction mixture is added with 50 ml of a normal solution of sodium cyanide in dimethylformamide. The mixture is maintained at room temperature for 3 hours while stirring, then hydrolyzed with 20 ml of methanol, and with pasty sodium sulfate. After purification of the so obtained α-aminonitrile by an acid-base extraction, there are obtained 0.350 g of 2-amino-2-phenyl acetonitrile, with a yield of 29%.

Workup

temperatureThe mixture is maintained at room temperature for 3 hours
customAfter purification of the so obtained α-aminonitrile
extractionby an acid-base extraction, there

Sources & evidence

ORD record: ord-e9b7a9e3737d4f69b68bd50534a0403f
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05103019

Reaction notes

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