Toluene → 2-Amino-4-cyano-4-ethoxy-butyronitrile
Reaction equation
[CH2:1]([O:3][C:4](=[CH2:7])[C:5]#[N:6])[CH3:2].[H-].C[Si]([C:13]#[N:14])(C)C.[Cl-].[NH4+:16].[C:17]1(C)C=CC=CC=1>O>[NH2:16][CH:17]([CH2:7][CH:4]([C:5]#[N:6])[O:3][CH2:1][CH3:2])[C:13]#[N:14]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
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 millimole of a toluene solution 1.5M of diisobutyauminum hydride (51.5 ml) are added, dropwise, at -60° C. After stirring at this temperature for 45minutes, 7.7 m (.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
- customat -60° C
- stirringwhile stirring
- customAfter purification of the so-obtained aminonitrile
Sources & evidence
- ORD record
- ord-4ead34aa25bd44d7bb630ff7c7645e6d
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05103019
Reaction notes
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