1: 3.5 g / hydrazine hydrate / ethane-1,2-diol / 140 deg C, 1 h then 195 deg C, 6 h 2: pyridine 3: 3.62 g / lead tetraacetate, iodine / CCl4 4: 1.5 g / Zn/HCl / dioxane 5: perchloric acid 6: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 7: 1.) Mg,I2 / 1 h, reflux 8: 0.675 g / pyridine / 0 °C 9: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 10: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

1: 1.) triethylamine; 2.) 25percent HCl / 1.) chloroform, 3 h, 35 deg C; 2.) 5 h, reflux 2: 85 percent / NaOH / methanol / 1 h / Heating 3: 3.5 g / hydrazine hydrate / ethane-1,2-diol / 140 deg C, 1 h then 195 deg C, 6 h 4: pyridine 5: 3.62 g / lead tetraacetate, iodine / CCl4 6: 1.5 g / Zn/HCl / dioxane 7: perchloric acid 8: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 9: 1.) Mg,I2 / 1 h, reflux 10: 0.675 g / pyridine / 0 °C 11: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 12: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

1: 1.5 g / Zn/HCl / dioxane 2: perchloric acid 3: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 4: 1.) Mg,I2 / 1 h, reflux 5: 0.675 g / pyridine / 0 °C 6: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 7: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

1: 3.62 g / lead tetraacetate, iodine / CCl4 2: 1.5 g / Zn/HCl / dioxane 3: perchloric acid 4: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 5: 1.) Mg,I2 / 1 h, reflux 6: 0.675 g / pyridine / 0 °C 7: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 8: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

1: 85 percent / NaOH / methanol / 1 h / Heating 2: 3.5 g / hydrazine hydrate / ethane-1,2-diol / 140 deg C, 1 h then 195 deg C, 6 h 3: pyridine 4: 3.62 g / lead tetraacetate, iodine / CCl4 5: 1.5 g / Zn/HCl / dioxane 6: perchloric acid 7: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 8: 1.) Mg,I2 / 1 h, reflux 9: 0.675 g / pyridine / 0 °C 10: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 11: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

sodium hydroxide; hydrogen bromide 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h; Yield given. Multistep reaction;

1: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 2: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme