PPA in chlorobenzene 25.5 h; Heating / reflux;

hydrogenchloride in ethanol 3 h; Heating;

hydrogenchloride; acetic acid; zinc

1: 1.) NaNO2, hydrochloric acid, 2.) hydrated CuSO4, anhyd. NaSO3, NaOAc. 3.) hydrochloric acid 2: 70 percent / NaOAc / acetic acid / 6 h 3: 85 percent / alkaline hydrolysis 4: 30 percent / NaOH / hexamethylphosphoric acid triamide / 5.5 h / 80 °C 5: Cu-quinoline View Scheme

1: 70 percent / NaOAc / acetic acid / 6 h 2: 85 percent / alkaline hydrolysis 3: 30 percent / NaOH / hexamethylphosphoric acid triamide / 5.5 h / 80 °C 4: Cu-quinoline View Scheme

1: 90 percent / NaBH4 / ethanol / 1 h / Heating 2: 88 percent / conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: 1.) NaNO3, hydrochloric acid, 2.) Na2S2, NaOH / 2.) H2O, room temperature, 2 h 2: 90 percent / Na2S2O4, Na2CO3 / H2O / 0.5 h / Heating 3: 70 percent / 1 h 4: 82 percent / anhyd. NaOAc / 1 h / Heating 5: 68 percent / 10percent NaOH / H2O / 1 h / Heating 6: 90 percent / NaBH4 / ethanol / 1 h / Heating 7: 88 percent / conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: 70 percent / 1 h 2: 82 percent / anhyd. NaOAc / 1 h / Heating 3: 68 percent / 10percent NaOH / H2O / 1 h / Heating 4: 90 percent / NaBH4 / ethanol / 1 h / Heating 5: 88 percent / conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: 90 percent / Na2S2O4, Na2CO3 / H2O / 0.5 h / Heating 2: 70 percent / 1 h 3: 82 percent / anhyd. NaOAc / 1 h / Heating 4: 68 percent / 10percent NaOH / H2O / 1 h / Heating 5: 90 percent / NaBH4 / ethanol / 1 h / Heating 6: 88 percent / conc. HCl / aq. ethanol / 3 h / Heating View Scheme

1: 68 percent / 10percent NaOH / H2O / 1 h / Heating 2: 90 percent / NaBH4 / ethanol / 1 h / Heating 3: 88 percent / conc. HCl / aq. ethanol / 3 h / Heating View Scheme