1: 1.) aq. KOH, 2.) quinoline / 1.) EtOH, reflux, 12h, 2.) reflux, 2 h 2: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, 4 h View Scheme

potassium hydroxide

1: 1.) aq. KOH, 2.) quinoline / 1.) EtOH, reflux, 12h, 2.) reflux, 2 h 2: 1.) n-BuLi / 1.) THF, RT, 2 h, 2.) THF, 4 h 3: 96 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) NaH / 1.) THF, 0 deg C, 2.) THF, from 55 deg C to 60 deg C, 5 h 5: 1.) aq. NaOH, 2.) 2N H2SO4 / 1.) EtOH, reflux, 8 h, 2.) reflux, 4 h View Scheme

quinoline; potassium hydroxide 1.) EtOH, reflux, 12h, 2.) reflux, 2 h; Yield given. Multistep reaction;

N-bromosuccinmide; trifluoroacetic acid in tetrahydrofuran T=20°C; 0.0833333 h;

copper(l) iodide; caesium carbonate in dimethyl sulfoxide T=50°C; 4 h; Inert atmosphere;

sulfuric acid T=4°C; 18 h; Heating / reflux;

sulfuric acid in ethanol 8 h; Heating;

ethanol Behandeln des Reaktionsprodukts mit aethanol. HCl;

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 2 h;