hydrogenchloride 16 h; Heating / reflux;

1.1: sodium hydride / tetrahydrofuran; mineral oil 1.2: 2 h / Reflux 2.1: nitric acid / 15 h / Reflux 3.1: sulfuric acid / 5 h / Reflux View Scheme

1: nitric acid / 15 h / Reflux 2: sulfuric acid / 5 h / Reflux View Scheme

1.1: 1 h / Reflux 2.1: hydrogen / palladium 10 on activated carbon / acetic acid / 760.05 Torr 3.1: hydrogenchloride; sodium nitrite / water / 0.17 h / 0 °C 3.2: 0.25 h 4.1: sodium t-butanolate / palladium diacetate; biphenyl-2-yl-di-tert-butyl-phosphane / toluene / 2 h / 95 °C / Inert atmosphere 5.1: potassium hydroxide / Reflux View Scheme

diisobutylaluminium hydride in dichloromethane; toluene T=-78 - 20°C; 3 h; Inert atmosphere;

palladium 10 on activated carbon; hydrogen in methanol P=760.051 Torr; 12 h;