palladium on activated charcoal; lithium 1.) liq. NH3-THF, 35 min 2.) tetralin, 210 deg C, 2 h; Yield given. Multistep reaction;

sodium hydride in diethyl ether; N,N-dimethyl-formamide 3 h;

hydrogenchloride in 1,4-dioxane 2.5 h; Heating;

1: 3 h / Heating 2: H2 / 10percent Pd-C / ethanol / 9.5 h / 80 °C 3: 81 percent / 2 h / 100 °C 4: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 5: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme

1: H2 / 10percent Pd-C / ethanol / 9.5 h / 80 °C 2: 81 percent / 2 h / 100 °C 3: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 4: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme

hydrogenchloride; hydrogen iodide; tin(ll) chloride 2.) MeOH, 3.) AcOH-THF; Yield given. Multistep reaction. Yields of byproduct given;

1: 88 percent / POCl3 / 6 h / 0 °C 2: 43 percent / POCl3 / 2 h / 60 °C 3: POCl3 / 6 h / 100 °C 4: 81 percent / 2 h / 100 °C 5: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 6: 53 percent / aq. HCl / dioxane / 2.5 h / Heating 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

1: 85 percent / PTSA / benzene / 2.5 h / Ambient temperature 2: 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 3: 88 percent / POCl3 / 6 h / 0 °C 4: 43 percent / POCl3 / 2 h / 60 °C 5: POCl3 / 6 h / 100 °C 6: 81 percent / 2 h / 100 °C 7: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 8: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme

1: 1.) sodium nitrite, aq. HCl 2.) 50percent aq. KOH / 1.)ice-cooled 2.) ethanol, below 7 deg C, 30 min 2: 85 percent / PTSA / benzene / 2.5 h / Ambient temperature 3: 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 4: 88 percent / POCl3 / 6 h / 0 °C 5: 43 percent / POCl3 / 2 h / 60 °C 6: POCl3 / 6 h / 100 °C 7: 81 percent / 2 h / 100 °C 8: 1.) NaBH4 2.) Na2CO3 / 1.) MeOH, RT, 2 h 2.) THF-water, RT, 1.5 h 9: 53 percent / aq. HCl / dioxane / 2.5 h / Heating View Scheme