1: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h 2: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C 3: 79 percent / 1 M NaOH / dioxane / 5 h / Ambient temperature View Scheme

With  hydrogen; nickel  1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h;  Yield given. Multistep reaction;   

Multi-step reaction with 2 steps 1: 1.) Raney nickel, 2.) Raney nickel, H2 / 1.) EtOH, 35 deg C, 24 h, 2.) RT, 40 psi, 1 h2: 1.) NaNO2, 80percent HOAc, 2.) NaN3 / 0 deg C