1: 1) thionylchloride 2) NH3 / 1) benzene, reflux, 45 min 2) H2O 2: phosphoryl chloride / 5 h / 100 °C 3: 98.5 percent / NaOH, H2O2 / 1) 40-60 deg C, 1 h 2) reflux, 4h 4: 76 percent / NaOH, Br2 / H2O / 0.75 h / 70 °C 5: 1) conc. HCl, NaNO2, 2) CuCl2/conc. HCl / 1) 10 deg C, 5 min 2) 5 deg C, 30 min, then RT, 1 h 6: 99 percent / HCl / ethanol / 1 h / Heating 7: 95 percent / polyphosphoric acid / 2.5 h / 120 °C 8: 65 percent / methanol 9: DDQ / dioxane View Scheme

1: 65 percent / dimethylaniline / 3 h / Heating 2: 86 percent / POCl3 / 2 h / Heating 3: 90 percent / NH3 / ethanol / 2 h 4: 76 percent / chromium(VI) oxide / acetic acid / 3 h 5: 61 percent / POCl3 / 2 h / Heating 6: 42 percent / H2, KOH / 10percent Pd/C / aq. ethanol / 1 h / 1551.4 Torr View Scheme