1: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme

1: 85 percent / ZnCl2 / benzene / 12 h / Heating 2: 70 percent / NBS, CaCl2 / benzene / 0.33 h / Irradiation 3: Raney Ni W2 / ethanol / 6 h 4: 90 percent / NH2NH2*H2O / acetonitrile / 6 h / Heating 5: 10 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 6: 98 percent / K2CO3 / acetonitrile / 2 h / Heating 7: 90 percent / ammonium formate / Pd/C / 1 h / Heating View Scheme

1: 72 percent / pyridine / 1.) 0 deg, 4 h, 2.) room temperature, overnight 2: 90 percent / triethyl ammonium iodide / 1.5 h / Heating 3: 90 percent / H2, Et3N / 10percent Pd/C / ethyl acetate / 760 Torr 4: 87 percent / 0.5percent NaOMe / methanol / 24 h / Ambient temperature 5: 80 percent / 92percent aq. hydrazine / ethanol / 0.75 h / Heating View Scheme

1: 100 percent / 92percent N2H4*H2O / ethanol / 0.08 h / Heating 2: 65 percent / SOCl2 3: 66 percent / pyridine / 0.5 h / 70 °C 4: 86 percent / Raneynickel / propan-2-ol / 3 h / Heating; also H2, 10percent Pd/C, NEt3, EtOAc investigated 5: 85 percent / 2M HCl / 2 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating  

Multi-step reaction with 2 steps 1: 75 percent / pyridine / 0 °C2: 90 percent / NaI / Heating