alpha-Formyl-3-(trifluoromethyl)benzeneacetonitrile → 3-Amino-2-[3-(trifluoromethyl)phenyl]-2-propenal
Reaction equation
[CH:1]([CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[C:4]#[N:5])=[O:2]>C(O)C>[NH2:5][CH:4]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)[CH:1]=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
portions of α-formyl-3-(trifluoromethyl)benzeneacetonitrile each in 250 ml. of ethanol are hydrogenated in the presence of 40 g. of Raney Nickel (number 28) at 20 psi pressure until no more hydrogen is absorbed. The resulting mixtures are filtered and the filtrates are combined and passed through 150 g. of alumina (Woelm, activity II) with 1:1 methylene chloride-ethyl acetate. The resulting eluate is concentrated at reduced pressure and the residue triturated with hexane to give 39.4 g. of the product of the Example as a yellow solid, m.p. 63°-70° C.