1: 61 percent 2: 85 percent / H2 / Pd-C 3: 1.) NaNO2, H2O/20percent H2SO4; 2.) Cu(NO3)2*3H2O/Cu2O / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 4: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 85 percent / H2 / Pd-C 2: 1.) NaNO2, H2O/20percent H2SO4; 2.) Cu(NO3)2*3H2O/Cu2O / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 3: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 61 percent 2: 85 percent / H2 / Pd-C 3: 1.) NaNO2, H2O/20percent H2SO4; 2.) Cu(NO3)2*3H2O/Cu2O / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 4: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

triethylamine in diethyl ether T=-10°C; 2 h; Yield given;

1: 1.) NaNO2, H2O/20percent H2SO4; 2.) Cu(NO3)2*3H2O/Cu2O / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 2: triethylamine / diethyl ether / 2 h / -10 °C View Scheme