tin(ll) chloride in acetic anhydride T=100°C; 12 h;

1: HNO3 2: H2 / Pd-C View Scheme

1: 92 percent / copper(II) nitrate trihydrate / acetic anhydride / 24 h / Ambient temperature 2: 87 percent / hydrazine monohydrate / Raney nickel / ethanol / 2.5 h / Heating; in the dark View Scheme

1: sodium, ethanol / xylene / 1 h / 100 °C 2: 92 percent / copper(II) nitrate trihydrate / acetic anhydride / 24 h / Ambient temperature 3: 87 percent / hydrazine monohydrate / Raney nickel / ethanol / 2.5 h / Heating; in the dark View Scheme

(i) aq. HCl, NaNO2, (ii) H3PO2; Multistep reaction;