1: thionyl chloride / dimethylformamide / benzene / 2 h / Heating 2: 72 percent / ammonia / CHCl3 / 1 h / Ambient temperature 3: 69 percent / sodium bis(2-methoxyethoxy)aluminum hyride, morpholine / toluene / 4 h / -15 °C 4: 73 percent / sodium methylate / dimethylformamide / 0.25 h / 75 °C 5: 59 percent / propan-2-ol / 0.5 h / Heating 6: 73 percent / sodium methylate / ethanol / 40 h / Heating View Scheme

1: thionyl chloride / dimethylformamide / benzene / 2 h / Heating 2: 72 percent / ammonia / CHCl3 / 1 h / Ambient temperature 3: 69 percent / sodium bis(2-methoxyethoxy)aluminum hyride, morpholine / toluene / 4 h / -15 °C 4: 73 percent / sodium methylate / dimethylformamide / 0.25 h / 75 °C 5: 59 percent / propan-2-ol / 0.5 h / Heating 6: 73 percent / sodium methylate / ethanol / 40 h / Heating 7: 55 percent / phosphorus oxychloride / pyridine / 3 h / 20 - 30 °C View Scheme