Ammonium Chloride → 2-Amino-4-cyano-4-ethoxy-butyronitrile

HRID 2165899Notes

Reaction equation

HRID 2165899 reaction equation
[CH2:1]([O:3][C:4](=[CH2:7])[C:5]#[N:6])[CH3:2].[H-].C([Al+]C[CH:15]([CH3:17])C)C(C)C.C[Si](C#[N:23])(C)C.[Cl-].[NH4+:25]>C1(C)C=CC=CC=1.O>[NH2:25][CH:17]([CH2:7][CH:4]([C:5]#[N:6])[O:3][CH2:1][CH3:2])[C:15]#[N:23]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 82115Trimethylsilyl cyanideHCID 123499402-Ethoxyprop-2-enenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 199011812-Amino-4-cyano-4-ethoxy-butyronitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-50 °C

Procedure

51.5 millimoles of ethoxy-acrylonitrile are dissolved in 10 ml of anhydrous toluene at 60° C. under an argon atmosphere. 77.25 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (51.5 ml) are added, dropwise, at -60° C. After stirring at this temperature for 45 minutes, 7.7 ml (1.1 eq) of trimethylsilyl cyanide are added to the reaction mixture at -50° C. The latter is maintained at -50° C. for 3 hours while stirring, then hydrolyzed by ammonium chloride then water. After purification of the so-obtained aminonitrile, by liquid chromatography on silica (elution with ethyl acetate/petroleum ether 1/1), 1.7 g of 2-amino-4-cyano-4-ethoxy-butyronitrile are obtained in a form of an orange-colored oil.

Workup

  1. customat -60° C
  2. stirringwhile stirring
  3. customAfter purification of the so-obtained aminonitrile

Sources & evidence

ORD record
ord-5c6369e4937c427f9a95e00dde322be6
Source dataset
uspto-grants-1990_07
Patent number
US04942221

Reaction notes

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