hydrogenchloride in ethanol; water Reflux;

1: pyridine, TiCl4 2: H2 / Raney-Ni 3: pyridinium chloride 4: 36percent aq. HCl / ethanol / 4 h / 80 °C View Scheme

1: pyridine, TiCl4 2: H2 / Raney-Ni 3: pyridinium chloride 4: 36percent aq. HCl / ethanol / 4 h / 80 °C View Scheme

1: H2 / Raney-Ni 2: pyridinium chloride 3: 36percent aq. HCl / ethanol / 4 h / 80 °C View Scheme

1.1: N,N,N',N,-tetramethylethylenediamine; n-butyllithium / hexane / 0.5 h / 0 - 60 °C 1.2: 0.5 h / 0 °C 2.1: pyridine; tetra-n-butylammonium tribromide / chloroform / 1 h / 20 °C 3.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl / toluene; ethanol / Inert atmosphere; Reflux 4.1: hydrogenchloride / ethanol; water / Reflux View Scheme

1: pyridine; tetra-n-butylammonium tribromide / chloroform / 1 h / 20 °C 2: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl / toluene; ethanol / Inert atmosphere; Reflux 3: hydrogenchloride / ethanol; water / Reflux View Scheme

1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl / toluene; ethanol / Inert atmosphere; Reflux 2: hydrogenchloride / ethanol; water / Reflux View Scheme

hydrogenchloride in ethanol T=80°C; 4 h;

1: pyridinium chloride 2: 36percent aq. HCl / ethanol / 4 h / 80 °C View Scheme