1: thionyl chloride; triethylamine / tetrahydrofuran / 0.33 h / 20 °C 2: 2.0 g / tetrahydrofuran / 2 h View Scheme

thionyl chloride 8 h; Inert atmosphereReflux;

1: 95 percent / LiAlH4 2: 86 percent / HBr / acetic acid View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 15 - 25 °C 2.1: triethylamine / dichloromethane / 2 h 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 3.2: 200 h / 0 - 80 °C / Inert atmosphere 3.3: pH 1 4.1: acetic acid / 1 h / 100 °C 4.2: 2 h / Reflux 5.1: hydrogen / Raney Ni / methanol / 6 h / 50 °C / 2206.72 Torr 6.1: acetic acid / ethanol / 4 h / Reflux 7.1: diethyl ether; tetrahydrofuran / 2.5 h / 25 °C 7.2: 3 h / Reflux 8.1: hydrogen / palladium 10 on activated carbon / methanol / 5 h / 70 °C / 3677.86 Torr View Scheme

1: thorium oxide / 430 - 450 °C 2: amalgamated zinc; aqueous HCl View Scheme

nitric acid

1: 62 percent / lithium aluminium hydride / tetrahydrofuran 2: 98 percent / pyridinium chlorochromate / CH2Cl2 View Scheme

1: 40 percent / Br2 / various solvent(s) / 5 h / 125 - 130 °C 2: 99 percent / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature View Scheme

tetrakis(triphenylphosphine) palladium(0); water; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in N,N-dimethyl-formamide T=80°C; 15 h; Inert atmosphere;

1: LiAlH4 / tetrahydrofuran / 0 °C / r.t., overnight 2: 90 percent / SOCl2 / 2 h / reflux View Scheme