in N,N-dimethyl-formamide T=120 - 140°C; 22 h;

1: 96 percent / HNO3 / acetic acid / 15 - 20 °C 2: 94 percent / K2CO3 / acetone / 6 h / Heating 3: 99 percent / H2 / 10 percent Pd/C / ethyl acetate 4: 64 percent / I2, aq. NaHCO3 / Ambient temperature 5: 1.) aq. NaNO2, H2SO4, 2.) Cu / 1.) 0 deg C, 30 min, 2.) EtOH, from 60 deg C to 75 deg C, 3 h 6: 83 percent / dimethylformamide / 22 h / 120 - 140 °C View Scheme

1: 94 percent / K2CO3 / acetone / 6 h / Heating 2: 99 percent / H2 / 10 percent Pd/C / ethyl acetate 3: 64 percent / I2, aq. NaHCO3 / Ambient temperature 4: 1.) aq. NaNO2, H2SO4, 2.) Cu / 1.) 0 deg C, 30 min, 2.) EtOH, from 60 deg C to 75 deg C, 3 h 5: 83 percent / dimethylformamide / 22 h / 120 - 140 °C View Scheme

1: 99 percent / H2 / 10 percent Pd/C / ethyl acetate 2: 64 percent / I2, aq. NaHCO3 / Ambient temperature 3: 1.) aq. NaNO2, H2SO4, 2.) Cu / 1.) 0 deg C, 30 min, 2.) EtOH, from 60 deg C to 75 deg C, 3 h 4: 83 percent / dimethylformamide / 22 h / 120 - 140 °C View Scheme

1: 64 percent / I2, aq. NaHCO3 / Ambient temperature 2: 1.) aq. NaNO2, H2SO4, 2.) Cu / 1.) 0 deg C, 30 min, 2.) EtOH, from 60 deg C to 75 deg C, 3 h 3: 83 percent / dimethylformamide / 22 h / 120 - 140 °C View Scheme

1: 1.) aq. NaNO2, H2SO4, 2.) Cu / 1.) 0 deg C, 30 min, 2.) EtOH, from 60 deg C to 75 deg C, 3 h 2: 83 percent / dimethylformamide / 22 h / 120 - 140 °C View Scheme