5 palladium on charcoal; hydrogen in methanol 24 h;

1.1: sodium tetrahydroborate; methanol / 3 h / 20 °C / Cooling with ice 1.2: 16 h / 20 °C 2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 4 h / 90 °C 3.1: sodium hydride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 3.2: 17 h / 20 °C / Cooling with ice 4.1: hydrogen bromide; acetic acid; phenol / 12 h / 75 °C / sealed tube; microwave irradiation 5.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 1 h 6.1: NH2NH2•xH2O / FeCl3·6H2O / methanol / 5 h / Reflux 6.2: 7 h / Reflux View Scheme

1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 4 h / 90 °C 2.1: sodium hydride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 2.2: 17 h / 20 °C / Cooling with ice 3.1: hydrogen bromide; acetic acid; phenol / 12 h / 75 °C / sealed tube; microwave irradiation 4.1: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 1 h 5.1: NH2NH2•xH2O / FeCl3·6H2O / methanol / 5 h / Reflux 5.2: 7 h / Reflux View Scheme

1: triethylamine; triphenylphosphine; di-tert-butylazodicarboxylate / toluene / 18 h / 20 °C / |Cooling with ice 2: 5 palladium on charcoal; hydrogen / methanol / 24 h View Scheme