hydrogen; nickel in ethanol; acetic acid 10 h;

1: 100 percent / conc. HNO3 / acetic acid / 1 h 2: 89 percent / H2 / Raney Nickel / ethanol; acetic acid / 10 h View Scheme

1: 84 percent / tetrabutylammonium iodide, KOH / tetrahydrofuran / 3 h / Heating 2: 100 percent / conc. HNO3 / acetic acid / 1 h 3: 89 percent / H2 / Raney Nickel / ethanol; acetic acid / 10 h View Scheme

1: 84 percent / tetrabutylammonium iodide, KOH / tetrahydrofuran / 3 h / Heating 2: 100 percent / conc. HNO3 / acetic acid / 1 h 3: 89 percent / H2 / Raney Nickel / ethanol; acetic acid / 10 h View Scheme

1.1: tetrabutylammomium bromide; sodium hydride / tetrahydrofuran / 0.17 h 1.2: 0.17 h 2.1: hydrazine hydrate; palladium 10 on activated carbon / tetrahydrofuran; ethanol; methanol / 1.08 h / 60 °C View Scheme