Procedure:  Parr bottle, Parr shaker

                  Dissolved 5.934 g of I in 130 mL of absolute EtOH.  Carefully added 3.001 g of 10% Pd/C.  The mixture was then hydrogenated at 50 psi for 45 min.  TLC (30:70 EtOAc-hexanes, UV) showed product spot at Rf 0.47.  The reaction mixture was then filtered through Celite and the solvent was removed by rotary evaporation.  The product was isolated by flash chromatography on silica using 30:70 EtOAc-hexanes as eluant.  The product was a white solid. 

 

¹H NMR (CDCl₃, 300 MHz) d 7.10 (dt, J = 7.7, 1.1 Hz, ArH, 1H), 7.03 (d, J = 7.7 Hz, ArH, 1H), 6.68 (m, ArH, 2H), 4.81 (br, NH, 1H), 4.23 (m, ArCH₂, NH₂, 4H), 1.44 (s, C(CH₃)₃, 9H).