hydrogenchloride in ethanol; water 2 h; Reflux;

1.1: hydrogenchloride; sodium nitrite / ethanol; water / 0.25 h / 0 °C 1.2: 2 h / 0 °C 2.1: hydrogenchloride / ethanol; water / 2 h / Reflux View Scheme

1: 24 h / 70 °C 2: 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene / acetonitrile / 5 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1.5 h / 190 °C / |Microwave irradiation View Scheme

1: 24 h / 70 °C 2: 1,5,7-triazabicyclo[4.4.0]dec-5-ene bound to polystyrene / acetonitrile / 5 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1.5 h / 190 °C / |Microwave irradiation View Scheme

potassium hydroxide

1: With sodium hydroxide in ethanol T=60°C; 2: With hydrogenchloride in ethanol pH=2;