hydrazine hydrate in ethanol 1 h; Heating;

1: 1.) pyridine, 2.) 0.1N NaOMe / 1.) 110 deg C, 18 h, 2.) MeOH 2: 91.3 percent / SOCl2 / 0.5 h / Heating 3: 79.3 percent / dimethylformamide / 12 h / 100 °C 4: 98.8 percent / hydrazine hydrate / aq. ethanol / 1 h / Heating View Scheme

1: 91.3 percent / SOCl2 / 0.5 h / Heating 2: 79.3 percent / dimethylformamide / 12 h / 100 °C 3: 98.8 percent / hydrazine hydrate / aq. ethanol / 1 h / Heating View Scheme

1: 79.3 percent / dimethylformamide / 12 h / 100 °C 2: 98.8 percent / hydrazine hydrate / aq. ethanol / 1 h / Heating View Scheme

1: 58.7 percent / Et3N / dimethylformamide / 0.5 h 2: 1.) pyridine, 2.) 0.1N NaOMe / 1.) 110 deg C, 18 h, 2.) MeOH 3: 91.3 percent / SOCl2 / 0.5 h / Heating 4: 79.3 percent / dimethylformamide / 12 h / 100 °C 5: 98.8 percent / hydrazine hydrate / aq. ethanol / 1 h / Heating View Scheme