1: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 2: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 3: 1.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 4: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 5: 71 percent / SOCl2 / benzene / 0.5 h / Heating 6: 89 percent / benzene / 1 h / Ambient temperature View Scheme

1: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 2: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 3: 90 percent / 10percent aq. NaOH / ethanol / 1 h / Heating View Scheme

1: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 2: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 3: 90 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 4: 87 percent / SOCl2 / benzene / 0.5 h / Heating View Scheme