1.1: water; zinc–copper couple; hydrogenchloride / methanol / 18 h / 25 °C 2.1: sodium carbonate; magnesium sulfate / ethanol; water / 23 h / 25 °C 3.1: toluene / 5 h / |Reflux 4.1: zinc; acetic acid / diethyl ether / 72 h / 0 - 25 °C 4.2: pH 7.2 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / |Inert atmosphere 5.2: 4 h / 0 - 20 °C / |Inert atmosphere 6.1: hydrogenchloride / water / 7 h / 20 °C 7.1: hydrogen; palladium 10 on activated carbon / methanol / 16 h / 7500.75 Torr 8.1: triethylamine / 48 h / 75 °C 9.1: water; acetic acid; sodium nitrite / 20 h / 25 °C 10.1: O-(6-chloro-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 25 °C / |Inert atmosphere 10.2: 16 h / 25 °C / |Inert atmosphere View Scheme

1.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C 2.1: sodium carbonate / methanol / 0.5 h / 25 °C 3.1: toluene / 5 h / |Reflux 4.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / |Inert atmosphere 5.2: 4 h / 0 - 20 °C / |Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr View Scheme

potassium hydroxide; hydrogen; palladium on activated charcoal in methanol 15 h; Ambient temperature;

1: 90 percent / KOH, H2 / 5percent Pd/C / methanol / 15 h / Ambient temperature 2: 1N HCl / H2O / 2 h / 110 °C 3: pyridine / 20 h / 20 °C View Scheme

1: 90 percent / KOH, H2 / 5percent Pd/C / methanol / 15 h / Ambient temperature 2: 1N HCl / H2O / 2 h / 110 °C 3: pyridine / 20 h / 20 °C 4: 65 percent / CF3SO2OSiMe3, hexamethyldisilazane / CH2Cl2 / 20 h / Ambient temperature 5: 97 percent / CH3ONa / methanol / Ambient temperature View Scheme

1: water; zinc–copper couple; hydrogenchloride / methanol / 18 h / 25 °C 2: sodium carbonate; magnesium sulfate / ethanol; water / 23 h / 25 °C 3: toluene / 5 h / |Reflux 4: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 30 °C / 2250.23 Torr View Scheme