1: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C 2: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating 3: p-TsOH / toluene / 12 h / Heating 4: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h 5: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C 6: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C 7: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h 8: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C 9: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C 10: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C 11: 40 percent / t-BuOK / 2 h / 20 °C View Scheme