1: 1.) triethylamine, 2.) HCl / 1.) ethanol, 90 min, room temp., 2.) ethanol 2: 91.1 percent / sodium nitrite, 2N HCl / H2O / first 0 deg C then room temperature, 2 h 3: 67.8 percent / 2N NaOH / ethanol / 2 h / Heating View Scheme

1: 1.) triethylamine, 2.) HCl / 1.) ethanol, 90 min, room temp., 2.) ethanol 2: 91.1 percent / sodium nitrite, 2N HCl / H2O / first 0 deg C then room temperature, 2 h 3: 67.8 percent / 2N NaOH / ethanol / 2 h / Heating 4: 55 percent / KOH powder / dimethylsulfoxide / 2 h / Ambient temperature View Scheme

C21H21ClIrNO2 in tetrahydrofuran; 2,2,2-trifluoroethanol 20 h; Inert atmosphere;

lithium borohydride; methyl iodide in tetrahydrofuran T=20°C; 0.25 h;

palladium on activated charcoal; sodium acetate; acetic acid T=60°C; P=1471.02 Torr; Hydrogenation;

1: POCl3 2: palladium/charcoal; acetic acid; sodium acetate / 60 °C / 1471.02 Torr / Hydrogenation View Scheme

palladium on activated charcoal 1) toluene, reflux, 1h, 2) ethanol, reflux, 30 min; Yield given. Multistep reaction;

T=200°C; im Rohr;