1: 1.) hydrazine hydrate, KOH, triethylene glycol 2.) KOH / 1.) a) 150 deg C, 2 h b) 200 deg C, 2,5 h 2.) DMSO, RT 2: 88 percent / POCl3 / 6 h / 0 °C 3: 43 percent / POCl3 / 2 h / 60 °C 4: POCl3 / 6 h / 100 °C 5: 81 percent / 2 h / 100 °C 6: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 7: 53 percent / aq. HCl / dioxane / 2.5 h / Heating 8: 1.) Li 2.) 10percent Pd-C / 1.) liq. NH3-THF, 35 min 2.) tetralin, 210 deg C, 2 h View Scheme

1: 1.) hydrazine hydrate, KOH, triethylene glycol 2.) KOH / 1.) a) 150 deg C, 2 h b) 200 deg C, 2,5 h 2.) DMSO, RT 2: 88 percent / POCl3 / 6 h / 0 °C 3: 43 percent / POCl3 / 2 h / 60 °C 4: POCl3 / 6 h / 100 °C 5: 81 percent / 2 h / 100 °C 6: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 7: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme