Nitrile and oxime

Nitriles and oximes are considered together because of common features. Both functions are reduced to primary amines, both undergo coupling reactions to secondary amines, and both are subject to reductive hydrolysis. These similarities arise from a common intermediate, an imine. The imine is... 

The C=N bonds of imines, oximes and hydrazones can be hydrogenated to form the corresponding amines even under ambient conditions on Pt, Pd, Rh and Raney Ni catalysts in acidic, neutral or basic media (equation 42). The imines, furthermore, are intermediates in the hydrogenation of nitro compounds, nitriles and oximes, and likewise play a key role as intermediates in the reductive amination of carbonyl compounds. 

Hydrogenation of a,6-unsaturated aldehydes on Raney zinc catalysts was studied. Saturated aldehydes were obtained along with saturated alcohols. The amounts of each were dependent on reaction conditions. On reduction of nitriles and oximes with Raney alloy improved yields of primary amines were obtained. Treatment of ketoximes with Raney-nickel yields the ketones. 

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