hydrogen; palladium on activated charcoal in methanol Ambient temperature;

1: 69 percent / KI / dimethylformamide / 12 h / Heating 2: 1.) hydrazine hydrate, 2.) 6N aq. HCl / 1.) 95percent EtOH, reflux, 0.5 h, 2.) MeOH, reflux, 1 h View Scheme

1: 87 percent / 4-toluenesulfonic acid / 5 h / Heating 2: 82 percent / K2CO3 / 14 h / Heating 3: H2O / 1 h / Heating 4: 78 percent / H2 / 10percent Pd/C / methanol / Ambient temperature View Scheme

1: 82 percent / K2CO3 / 14 h / Heating 2: H2O / 1 h / Heating 3: 78 percent / H2 / 10percent Pd/C / methanol / Ambient temperature View Scheme

hydrogenchloride; hydrazine hydrate 1.) 95percent EtOH, reflux, 0.5 h, 2.) MeOH, reflux, 1 h; Yield given. Multistep reaction;