Procedure: Parr Shaker, Parr bottle

                  Dissolved 3.797 g of nitrile I in 175 mL of absolute EtOH.  Carefully added 3.065 g of 10% Pd/C.  The reaction mixture was hydrogenated at 50 psi for 16 h.  TLC (4:96 Et₃N-MeOH, UV) shows product spot at Rf 0.56.  The reaction mixtrue was filtered through Celite and the solvent was removed by rotary evaportion.  The material was purified by flash chromatography on silica gel using 4:96 Et₃N-MeOH as eluant.  The product was a clear, colorless oil. 

 

¹H NMR (CDCl₃, 300 MHz) d 9.46 (s, NH, 1H), 7.97 (d, J = 7.7 Hz, ArH, 1H), 7.26 (dd(apparent t), J = 7.1 Hz, ArH, 1H), 7.09 (d, J = 7.7 Hz, ArH, 1H), 6.94 (m, ArH, 1H), 3.96 (s, ArCH₂, 2H), 1.71 (s, NH₂, 2H), 1.53 (s, C(CH₃)₃, 9H). 

 

notes

 

Possible side products may be observed due to transimination of the intermediate imine with the primary amine product to give secondary or even tertiary amines.