thionyl chloride 8 h; Inert atmosphereReflux;

1.1: NaNO2; aq. HCl 1.2: copper(I) cyanide / H2O / 0.33 h / 20 °C 2.1: 70 percent H2SO4 / 70 °C 3.1: sodium peroxide / H2O / 1 h / 20 °C 4.1: SOCl2 / 12 h / Heating View Scheme

1: 70 percent H2SO4 / 70 °C 2: sodium peroxide / H2O / 1 h / 20 °C 3: SOCl2 / 12 h / Heating View Scheme

1: sodium peroxide / H2O / 1 h / 20 °C 2: SOCl2 / 12 h / Heating View Scheme

1: (i) Mg, (ii) /BRN= 1900390/ 2: SOCl2 View Scheme

ammonium hydroxide

in tetrahydrofuran 2 h;

1.1: triethylamine / dichloromethane / 2 h 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 2.2: 200 h / 0 - 80 °C / Inert atmosphere 2.3: pH 1 3.1: acetic acid / 1 h / 100 °C 3.2: 2 h / Reflux 4.1: hydrogen / Raney Ni / methanol / 6 h / 50 °C / 2206.72 Torr 5.1: acetic acid / ethanol / 4 h / Reflux 6.1: diethyl ether; tetrahydrofuran / 2.5 h / 25 °C 6.2: 3 h / Reflux 7.1: hydrogen / palladium 10 on activated carbon / methanol / 5 h / 70 °C / 3677.86 Torr View Scheme

quinoline; sulfur; xylene Hydrogenation.Reagens 4: Palladium-Bariumsulfat-Katalysator;

T=128°C; Hydrogenation;