methanol; sodium hydroxide; hydrazine hydrate; diethylene glycol T=115°C; Erhitzen des Reaktionsprodukts auf 195grad;

potassium ethanolate

1: 1.) Br2, 48percent HBr / 1.) AcOH, ice-cooling, 30 min, 2.) THF, reflux, 4 h 2: 43 percent / pyridine / 48 h View Scheme

1: 1.) Br2, 48percent HBr / 1.) AcOH, ice-cooling, 30 min, 2.) THF, reflux, 4 h 2: 1.) NaNO2, 40percent H2SO4; 2.) CuSO4.5H2O, NaCl / 1.) water, -12 deg C, 2 h; 2.) water, -2 deg C, 2 h, room temperature 3: 98 percent / hydrogen chloride / ice-cooling 4: 99 percent / H2, triethylamine / 10percent Pd-C / ethanol 5: 78 percent / methanol 6: 88 percent / p-TsOH / toluene / 4 h / Heating View Scheme