hydrogenchloride in nitromethane T=0 - 20°C; 0.75 h;

methanol; potassium permanganate in acetonitrile T=25°C; 0.5 h;

1: 72 percent / H2 / 10percent Pd/C / dimethylformamide / 12 h / 735.5 Torr / Ambient temperature 2: 87 percent / HCl gas / nitromethane / 0.75 h / 0 - 20 °C View Scheme

I2 Yield given. Multistep reaction;

1: zinc / acetic acid / 4 h / 25 °C 2: 92 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 3: 74 percent / 95percent hydrazine hydrate / methanol / 72 h / Heating 4: 4 h / Heating 5: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 6: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 7: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 8: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 77 percent / 1N NaOH / dimethylformamide; methanol / 18 h / 60 °C 2: zinc / acetic acid / 4 h / 25 °C 3: 92 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 4: 74 percent / 95percent hydrazine hydrate / methanol / 72 h / Heating 5: 4 h / Heating 6: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 7: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 8: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 9: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 98 percent / tetrahydrofuran / 4 h / Heating 2: 77 percent / 1N NaOH / dimethylformamide; methanol / 18 h / 60 °C 3: zinc / acetic acid / 4 h / 25 °C 4: 92 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 5: 74 percent / 95percent hydrazine hydrate / methanol / 72 h / Heating 6: 4 h / Heating 7: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 8: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 9: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 10: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 4 h / Heating 2: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 3: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 4: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 5: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 92 percent / pyridine, hydroxylamine hydrochloride / methanol / 1 h / Heating 2: 74 percent / 95percent hydrazine hydrate / methanol / 72 h / Heating 3: 4 h / Heating 4: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 5: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 6: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 7: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme

1: 74 percent / 95percent hydrazine hydrate / methanol / 72 h / Heating 2: 4 h / Heating 3: 1N HCl / trifluoroacetic acid / 0.33 h / 60 - 65 °C 4: sodium dithionite / dimethylformamide; H2O / 2 h / 60 - 65 °C 5: 0.1 N NaOH, / acetonitrile / 18 h / 25 °C 6: MeOH, 5percent KMnO4 / acetonitrile / 0.5 h / 25 °C View Scheme