hydrazine hydrate in diethylene glycol T=180°C; 4 h;

1: 1.) 2.6 M n-BuLi, 2.) fluoropicoline / 1.) diethyl ether, -65 deg C, 1 h, 2.) diethyl ether, -40 deg C to -30 deg C, 30 min 2: 60 percent / potassium permanganate / H2O / 1.75 h / Heating 3: 85 percent / polyphosphoric acid / 4.5 h / 210 °C 4: 80 percent / hydrazine monohydrate / bis-(2-hydroxy-ethyl) ether / 4 h / 180 °C View Scheme

1: 60 percent / potassium permanganate / H2O / 1.75 h / Heating 2: 85 percent / polyphosphoric acid / 4.5 h / 210 °C 3: 80 percent / hydrazine monohydrate / bis-(2-hydroxy-ethyl) ether / 4 h / 180 °C View Scheme

1: 85 percent / polyphosphoric acid / 4.5 h / 210 °C 2: 80 percent / hydrazine monohydrate / bis-(2-hydroxy-ethyl) ether / 4 h / 180 °C View Scheme

1: 1.) 2.6 M n-BuLi, 2.) fluoropicoline / 1.) diethyl ether, -65 deg C, 1 h, 2.) diethyl ether, -40 deg C to -30 deg C, 30 min 2: 60 percent / potassium permanganate / H2O / 1.75 h / Heating 3: 85 percent / polyphosphoric acid / 4.5 h / 210 °C 4: 80 percent / hydrazine monohydrate / bis-(2-hydroxy-ethyl) ether / 4 h / 180 °C View Scheme