1: 98 percent / NaN3 2: 92 percent / H2 / Pd View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1.5 h / Reflux 1.2: 20 °C 2.1: palladium 10 on activated carbon; hydrogen / ethanol / 70 °C / 52505.3 Torr / Continuous-flow conditions View Scheme

hydrogenchloride; ethanol

T=205°C;

1: 55 percent / Na2CO3 / 36 h / 110 °C 2: 49 percent Spectr. / toluenesulphonyl chloride, NaOH / dioxane / 5 h / 60 °C / variation of base View Scheme

1: 1-hydroxybenzotriazole, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature 2: pyridine / CH2Cl2 / 12 h / 0 - 20 °C 3: K2CO3, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C 4: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C 5: formic acid, H2 / 10percent Pd/C / methanol / 3 h / 760 Torr 6: ethanol / 24 h / 80 °C 7: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature 8: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature View Scheme

sodium carbonate T=110°C; 36 h;

1: sodium hydrogencarbonate / water / Inert atmosphere 2: sodium hypochlorite; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / Inert atmosphere View Scheme

1: dichloromethane 2: sodium hydroxide / tetrahydrofuran; toluene / 45 °C 3: hydrogenchloride; water / 1 h 4: potassium carbonate / water / 16.75 h / 20 °C View Scheme

potassium hydroxide in 1,4-dioxane; water 1) 0 deg C, 1 h, 2) room temp., 4 h;