hydrogenchloride; water in water 16 h; Reflux;

hydrogenchloride; hydrazine hydrate in ethanol Heating;

1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 6: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 5: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1: 240 g / Zn / benzene / Heating 2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 3: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 4: 16 percent / NH3 / tetrahydrofuran / 3 h 5: 65 percent / 1 M NH4OH / 1 h / 70 °C 6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 7: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1.1: cesium fluoride; tetrabutyl-ammonium chloride; bis-triphenylphosphine-palladium(II) chloride / toluene; water / 18 h / 20 °C / |Inert atmosphere 2.1: acetic acid / chloroform / 1 h / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 4.1: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C 5.1: hydrogenchloride; water / water / 16 h / |Reflux View Scheme

1: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 2: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1: 65 percent / 1 M NH4OH / 1 h / 70 °C 2: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 3: 54 percent / 6 M HCl / 2 h / Heating View Scheme

1: 16 percent / NH3 / tetrahydrofuran / 3 h 2: 65 percent / 1 M NH4OH / 1 h / 70 °C 3: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 4: 54 percent / 6 M HCl / 2 h / Heating View Scheme

aluminum oxide in toluene 16 h; Heating / reflux;