hydrazine hydrate in ethanol T=80°C; 0.75 h;

1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 1.2: 1 h / 20 °C 2.1: hydrazine hydrate / ethanol / 6 h / |Reflux View Scheme

1.1: thionyl chloride / ethanol / 5.5 h / -10 °C / |Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 2.2: 1 h / 20 °C 3.1: hydrazine hydrate / ethanol / 6 h / |Reflux View Scheme

1: hydrogenchloride; sodium nitrite; tin(ll) chloride / -5 - 20 °C 2: acetic acid / ethanol / 1 h / 80 °C 3: polyphosphoric acid / toluene / 5 h / 100 °C 4: sodium hydride / tetrahydrofuran / 0.67 h / 0 °C 5: hydrazine hydrate / ethanol / 0.75 h / 80 °C View Scheme

1: acetic acid / ethanol / 1 h / 80 °C 2: polyphosphoric acid / toluene / 5 h / 100 °C 3: sodium hydride / tetrahydrofuran / 0.67 h / 0 °C 4: hydrazine hydrate / ethanol / 0.75 h / 80 °C View Scheme

1: polyphosphoric acid / toluene / 5 h / 100 °C 2: sodium hydride / tetrahydrofuran / 0.67 h / 0 °C 3: hydrazine hydrate / ethanol / 0.75 h / 80 °C View Scheme

trichlorophosphate 1.) dioxane, room temp., 30 min; 2.) ca. 10 deg C -> 60 deg C; Yield given. Multistep reaction;