potassium iodide in N,N-dimethyl-formamide 1 h; Heating;

1: 25.3 g / Et3N, bis(triphenylphosphine)palladiumdichloride / CH2Cl2 / 3 h / Heating 2: 84 percent / H2 / Pd-C / ethanol 3: 22.3 g / SOCl2 / CH2Cl2 / room temperature, 1 h -> reflux 1 h 4: 71 percent / KI / dimethylformamide / 1 h / Heating View Scheme

1: 84 percent / H2 / Pd-C / ethanol 2: 22.3 g / SOCl2 / CH2Cl2 / room temperature, 1 h -> reflux 1 h 3: 71 percent / KI / dimethylformamide / 1 h / Heating View Scheme

1: 22.3 g / SOCl2 / CH2Cl2 / room temperature, 1 h -> reflux 1 h 2: 71 percent / KI / dimethylformamide / 1 h / Heating View Scheme

hydrazine hydrate in ethanol 3 h; Heating;