quinoline; hydrogen; Lindlar's catalyst in ethanol 4 h;

1.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C 1.2: 98 percent / CH2Cl2; hexane / -78 - 20 °C 2.1: 83 percent / H2; quinoline / Lindlar catalyst / ethanol / 4 h View Scheme

1: cyclohexylMgCl With copper(l) iodide in tetrahydrofuran T=-60°C; 0.75 h; 2: acetylene in tetrahydrofuran T=-60 - -20°C; 3: carbon dioxide With phosphorous acid trimethyl ester in tetrahydrofuran T=-50 - 20°C; 5 h; Further stages.;

1: With lithium hydroxide hydrate in tetrahydrofuran; water T=70°C; 15 h; 2: With hydrogenchloride in tetrahydrofuran; water T=0°C; pH=1 - 2; Overall yield = 1.48 g;

benzophenone 2.5 h; Irradiation; Title compound not separated from byproducts;