1.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 2.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 4.2: 3 h / 20 °C 5.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 6.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C 7.1: triethylamine; sodium iodide / 1,4-dioxane / 7 h / 120 °C 8.1: sodium nitrite / water; acetic acid; ethyl acetate / 30 °C 9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h 10.1: hydrogenchloride; water / methanol / 1 h View Scheme

1.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 2.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C 4.2: 3 h / 20 °C 5.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C 6.1: 5 Pd(II)/C(eggshell) / methanol / 1 h / 20 °C View Scheme

1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C View Scheme

1: 730 mg / chlorobenzene / 135 °C 2: 98 percent / hydrogen; HCO2NH4 / Pd/C / methanol / 2 h / 20 °C View Scheme

Multi-step reaction with 6 steps 1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C2: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C3: triethylamine; sodium iodide / 1,4-dioxane / 120 °C4: sodium nitrite / water; acetic acid; ethyl acetate5: N-ethyl-N,N-diisopropylamine / dichloromethane6: hydrogenchloride; water / methanol; water  

Multi-step reaction with 5 steps 1.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C2.1: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C3.1: N-ethyl-N,N-diisopropylamine / isobutyl methylketone / 2 h / 20 °C4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C4.2: 3 h / 20 °C5.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C