1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h 2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr View Scheme

1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h 2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=4°C; Reflux;

hydrogen; palladium dihydroxide in ethyl acetate T=20°C; P=760 Torr;

diisobutylaluminium hydride in toluene T=-70°C;

trifluoroacetic acid T=19°C; some hours, Var.: heating;

1: 93 percent / K2CO3 / acetone / 12 h / Heating 2: 99 percent / LiAlH4 / diethyl ether / 0.5 h 3: 90 percent / H2 / 20 percent Pd(OH)2/C / ethyl acetate / 20 °C / 760 Torr View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 0.5 h 2: 90 percent / H2 / 20 percent Pd(OH)2/C / ethyl acetate / 20 °C / 760 Torr View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 1 h; Ambient temperature;