1: 98 percent / NaOAc / <Pd(dppp)2Cl2> / dimethylformamide / 140 °C / 79800 Torr 2: NBS, (BzO)2 / CCl4 / Irradiation 3: 5percent H2SO4 / Heating 4: 100 percent / tetrahydrofuran / -78 °C 5: 80 percent / t-BuOK / 1,2-dimethoxy-ethane / 12 h / 50 °C 6: t-BuOK / dimethylformamide / 25 °C 7: SeO2/SiO2, t-BuOOH, AcOH / 110 °C 8: 10percent aq. H2SO4 / Heating 9: NaBH4, CeCl3 / ethanol / 1.) 0 deg C, 20 min, 2.) 45 deg C, 30 min 10: 60percent H2SO4 / ethanol / 5 h / 115 °C View Scheme

phosphorus pentachloride in various solvent(s) T=150°C; 4 h; variation of temperatures and solvents; also other methylquinolines as substrates;

acetamide; potassium carbonate T=200°C; 3 h;

acetic acid; zinc in water T=75°C; 1 h;

1: 98 percent / NaOAc / <Pd(dppp)2Cl2> / dimethylformamide / 140 °C / 79800 Torr 2: NBS, (BzO)2 / CCl4 / Irradiation 3: 5percent H2SO4 / Heating 4: 100 percent / tetrahydrofuran / -78 °C 5: t-BuOK / 1,2-dimethoxy-ethane / 12 h / 50 °C 6: t-BuOK / dimethylformamide / 25 °C 7: SeO2/SiO2, t-BuOOH, AcOH / 110 °C 8: 10percent aq. H2SO4 / Heating 9: NaBH4, CeCl3 / ethanol / 1.) 0 deg C, 20 min, 2.) 45 deg C, 30 min 10: 60percent H2SO4 / ethanol / 5 h / 115 °C View Scheme