Sodium Sulfate → 2-Amino-4-phenyl-3-butenenitrile

HRID 2165898Notes

Reaction equation

[C:1](#[N:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C.C[Si]([C:25]#[N:26])(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[NH2:10][CH:1]([CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:25]#[N:26]

Participants

Conditions

Temperature: -40 °C

Procedure

10 millimoles (1.29 g) of cinnamonitrile are dissolved in 150 ml of anhydrous toluene at -70° C., under an argon atmosphere. 15 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (10 ml) are added, dropwise, at -70° C. The stirring is maintained at this temperature for 30 minutes, then 2 ml of trimethylsilyl cyanide are added at -40° C. The stirring is then maintained at -40° C. for 2 hours. The reaction mixture is then hydrolyzed at -20° C. with 10 ml methanol and with pasty sodium sulfate. The so-obtained product is purified by liquid chromatography on silica, in eluting with ethyl acetate/petroleum ether 1/1. There are obtained 0.515 g of purified 2-amino-4-phenyl-3-butene-nitrile; yield 33%.

Workup

customat -70° C
temperatureThe stirring is maintained at this temperature for 30 minutes
customhydrolyzed at -20° C.
customThe so-obtained product is purified by liquid chromatography on silica
washin eluting with ethyl acetate/petroleum ether 1/1

Sources & evidence

ORD record: ord-eadbfacd2b454fc8bde720b5a5e59df0
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04942221

Reaction notes

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