1: 1.) 6 N HCl, NaNO2; 2.) CuCl2 / 1.) H2O, -5 deg C, 1 h; 2.) H2O, 50-55 deg C 2: 89 percent / conc. H2SO4 / 7 h / Heating 3: 83 percent / hydrogen / 10percent Pd-C / acetic acid / Ambient temperature 4: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 5: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 6: 1.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 7: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 8: 71 percent / SOCl2 / benzene / 0.5 h / Heating 9: 89 percent / benzene / 1 h / Ambient temperature View Scheme

1: 89 percent / conc. H2SO4 / 7 h / Heating 2: 83 percent / hydrogen / 10percent Pd-C / acetic acid / Ambient temperature 3: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 4: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 5: 1.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 6: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 7: 71 percent / SOCl2 / benzene / 0.5 h / Heating 8: 89 percent / benzene / 1 h / Ambient temperature View Scheme

1: 83 percent / hydrogen / 10percent Pd-C / acetic acid / Ambient temperature 2: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 3: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 4: 1.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 5: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 6: 71 percent / SOCl2 / benzene / 0.5 h / Heating 7: 89 percent / benzene / 1 h / Ambient temperature View Scheme

1: 1.) 6 N HCl, NaNO2; 2.) CuCl2 / 1.) H2O, -5 deg C, 1 h; 2.) H2O, 50-55 deg C 2: 89 percent / conc. H2SO4 / 7 h / Heating 3: 83 percent / hydrogen / 10percent Pd-C / acetic acid / Ambient temperature 4: 1.) 6 N HCl, NaNO2; 2.) NaN3 / 1.) -5 deg C, 1 h; 2.) H2O, r.t. 5: 70 percent / o-dichlorobenzene / 1 h / 160 - 170 °C 6: 1.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 7: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 8: 71 percent / SOCl2 / benzene / 0.5 h / Heating 9: 89 percent / benzene / 1 h / Ambient temperature View Scheme

in benzene 1 h; Ambient temperature;

1: 71 percent / SOCl2 / benzene / 0.5 h / Heating 2: 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: 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.) NaH / 1.) dimethylformamide, 1 h, r.t.; 2.) dimethylformamide, 2 h, r.t. 2: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 3: 71 percent / SOCl2 / benzene / 0.5 h / Heating 4: 89 percent / benzene / 1 h / Ambient temperature View Scheme

1: 88 percent / 10percent aq. NaOH / ethanol / 1 h / Heating 2: 71 percent / SOCl2 / benzene / 0.5 h / Heating 3: 89 percent / benzene / 1 h / Ambient temperature View Scheme

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