thionyl chloride 2 h; Reflux;

1: 68 percent / n-BuLi / -78 °C 2: SOCl2 / 2 h / Heating View Scheme

1: diethyl ether 2: gl. AcOH / 1.5 h View Scheme

1: aq. KOH, CH2N2 / diethyl ether; various solvent(s) / 0.75 h / Ambient temperature 2: glacial AcOH / 0.5 h / Ambient temperature 3: 71 percent / xylene / 72 h / Heating 4: 98 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 5: 82.5 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature 6: 51 percent / hydrazine hydrate / ethanol / 3 h / Heating View Scheme

quinoline; Pd-BaSO4; sulfur Hydrogenation.Reagens 4: Xylol;

in dichloromethane T=20°C; 12 h; Inert atmosphere;

3: acetic acid; aqueous hydrochloric acid View Scheme

1: 64.9 percent / AlCl3 / 1) ether, reflux, 1h, 2) r.t., 24h 2: 91.5 percent / pyridine, tetramethylammoniumhydroxid / H2O / 24 h / Heating View Scheme

aluminium trichloride 1) ether, reflux, 1h, 2) r.t., 24h;

3: acetic acid; aqueous hydrochloric acid 4: aqueous sulfuric acid View Scheme