1: 75 percent / 98percent hydrazine hydrate / 10percent palladium on charcoal / ethanol; dioxane / 70 °C 2: 1.) NaNO2, conc. HCl; 2.) cuprous chloride / 1.) water, (-5) - 0 deg C; 2.) room temp., 120 min. View Scheme

1: 65 percent / hydroxylamine hydrochloride, potassium hydroxide / ethanol; dioxane; methanol / 1.) 0 deg C, 0.5 h, 2.) RT, 1 h 2: 80 percent / hydrazine hydrate, 10 percent Pd/C / ethanol; dioxane / Heating View Scheme