1: 95 percent / H2 / 5percent Pd/C / acetic acid 2: 86 percent / dimethylformamide / 3 h / Heating 3: 92 percent / diisobutylaluminium hydride / toluene / 2 h / 45 °C 4: 97 percent / hydrazine monohydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 1.) 80 deg C, 1 h, 2.) reflux, 2 h 5: 88 percent / acetic anhydride / 2 h / Heating View Scheme

1: 68 percent / H2, / PtO2, / acetic acid / Ambient temperature 2: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H2O, reflux, 2 h, 3: 25 percent / hexamethylphosphoric acid triamide / 7 h / 160 °C View Scheme

hydrogenchloride; ammonium hydroxide; bromine; aluminium trichloride; Zinc chloride in water; 1,2-dichloro-ethane

hydrogenchloride; bromine; magnesium sulfate; aluminium trichloride; Zinc chloride in dichloromethane; water; 1,2-dichloro-ethane; toluene

aluminium trichloride; bromine in dichloromethane T=60°C; 3 h;

hydrogen; palladium on activated charcoal in acetic acid

1: 68 percent / H2, / PtO2, / acetic acid / Ambient temperature 2: 2.) PPA, 3.) cc HCl, / 1.) 150 deg C, 1 h, 2.) 150 deg C, 30 min, 3.) AcOH, H2O, reflux, 2 h, 3: 30 percent / hexamethylphosphoric acid triamide / 6 h / 160 °C View Scheme