1: 63.4 percent / K2CO3 / acetone / 5 h / Heating 2: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 3: 89.8 percent / H2 / 5percent Pd-C / ethanol 4: 1.) NaNO2, H2O/7.3percent H2SO4 / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 5: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 98.6 g / NaH / dimethylformamide / 24 h / 44 - 47 °C 2: 63.4 percent / K2CO3 / acetone / 5 h / Heating 3: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 4: 89.8 percent / H2 / 5percent Pd-C / ethanol 5: 1.) NaNO2, H2O/7.3percent H2SO4 / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 6: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 89.8 percent / H2 / 5percent Pd-C / ethanol 2: 1.) NaNO2, H2O/7.3percent H2SO4 / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 3: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 2: 89.8 percent / H2 / 5percent Pd-C / ethanol 3: 1.) NaNO2, H2O/7.3percent H2SO4 / 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/7.3percent H2SO4 / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 2: triethylamine / diethyl ether / 2 h / -10 °C View Scheme