quinoline; copper T=220°C; 3 h;

1: 90 percent / sodium azide, acetic acid / aq. ethanol / 0 °C 2: 65 percent / sodium borohydride / ethanol / Ambient temperature 3: 75 percent / methanesulphonyl chloride, pyridine / dimethylformamide / 1 h / 80 °C 4: 75 percent / xylene / 0.25 h / Heating View Scheme

1: xylene / 120 - 125 °C 2: aq. KOH / bis-(2-hydroxy-ethyl) ether / 195 °C View Scheme

1: NaOEt / ethanol / 1 h / Heating 2: aq. KOH / 2 h / Heating 3: Cu*Cr2O3 / quinoline / 0.5 h / 160 °C View Scheme

1: aq. KOH / 2 h / Heating 2: Cu*Cr2O3 / quinoline / 0.5 h / 160 °C View Scheme