hydrogenchloride; sodium nitrite T=0°C; 2 h;

1: 72 percent / NaNO2, 2N aq. HCl / 2 h / 0 °C 2: 94 percent / 1N aq. NaOH / methanol / 2.5 h / Ambient temperature View Scheme

1: sodium nitrite; hydrochloric acid / 0 °C 2: 53 percent / zinc; glacial acetic acid / Heating View Scheme

sodium hydroxide in methanol; water T=20 - 25°C; 3.5 h;

1: 69 percent / sodium methoxide / methanol / Ambient temperature 2: PdCl2(PhCN)2 / tetrahydrofuran / 8 h / Ambient temperature 3: 79 percent / conc. H2SO4, 2-allyl-3-thio-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione / formic acid / 1 h / Heating View Scheme

water; hydrazine hydrate; butan-1-ol

sodium in ethanol 1 h; Reflux;