1: H2SO4 2: sodium; xylene 3: acetic acid; amalgamated zinc; aqueous HCl View Scheme

1: N2H4+H2O; KOH; diethylene glycol 2: H2SO4 3: sodium; xylene 4: acetic acid; amalgamated zinc; aqueous HCl View Scheme

1: AlCl3; CS2 2: N2H4+H2O; KOH; diethylene glycol 3: H2SO4 4: sodium; xylene 5: acetic acid; amalgamated zinc; aqueous HCl View Scheme

hydrogenchloride; Zn–Hg amalgam; acetic acid

1: 70.9 percent / AlCl3 / CS2 / 1.) 5 h, room temperature, 2.) 30 min., 40-50 deg C 2: 56.7 percent / Na2S / tetrahydrofuran; ethanol / Heating 3: 60.6 percent / sodium methoxide / dioxane; methanol / 1.) 12 h, room temperature, 2.) 30 min., heating other solvent: EtOH 4: 91 percent / ethylene glycol, hyrazine hydrate / dioxane / 0.5 h / Heating 5: 90.2 percent / Raney nickel W-2 / dioxane / 1 h / Heating View Scheme

1: 56.7 percent / Na2S / tetrahydrofuran; ethanol / Heating 2: 60.6 percent / sodium methoxide / dioxane; methanol / 1.) 12 h, room temperature, 2.) 30 min., heating other solvent: EtOH 3: 91 percent / ethylene glycol, hyrazine hydrate / dioxane / 0.5 h / Heating 4: 90.2 percent / Raney nickel W-2 / dioxane / 1 h / Heating View Scheme

1: 91 percent / ethylene glycol, hyrazine hydrate / dioxane / 0.5 h / Heating 2: 90.2 percent / Raney nickel W-2 / dioxane / 1 h / Heating View Scheme

1: 60.6 percent / sodium methoxide / dioxane; methanol / 1.) 12 h, room temperature, 2.) 30 min., heating other solvent: EtOH 2: 91 percent / ethylene glycol, hyrazine hydrate / dioxane / 0.5 h / Heating 3: 90.2 percent / Raney nickel W-2 / dioxane / 1 h / Heating View Scheme