1: 88 percent / NH2OH*HCl, Na2CO3 / ethanol / Ambient temperature 2: 91 percent / NaOEt / ethanol / Ambient temperature 3: 97 percent / NaH / dimethylformamide / 100 °C 4: 98 percent / NH2NH2*H2O / ethanol / Heating 5: 48 percent / Na2S2O4 / dimethylformamide; H2O / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); hydrogen; palladium on activated charcoal in acetic acid; ethyl acetate T=20°C; P=760 Torr; 3 h;

1: 63.4 percent / K2CO3 / acetone / 5 h / Heating 2: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 3: 89.8 percent / H2 / 5percent Pd-C / ethanol 4: 95 percent / NH4SCN / acetone / 1 h / Ambient temperature View Scheme

1: 63.4 percent / K2CO3 / acetone / 5 h / Heating 2: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 3: 89.8 percent / H2 / 5percent Pd-C / ethanol 4: 99.3 percent / CH2Cl2 / 1 h / Ambient temperature 5: 11.0 g / Na2CO3 / dimethylformamide / 2.5 h / Ambient temperature 6: 4.8percent aq. NaOH / benzene; dimethylformamide; H2O / 1 h / 8 °C 7: 70 percent / NH4SCN / acetone / 1 h / Ambient temperature View Scheme

1: 63.4 percent / K2CO3 / acetone / 5 h / Heating 2: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 3: 89.8 percent / H2 / 5percent Pd-C / ethanol 4: 1.) NaNO2, H2O/7.3percent H2SO4 / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min 5: triethylamine / diethyl ether / 2 h / -10 °C View Scheme

1: 63.4 percent / K2CO3 / acetone / 5 h / Heating 2: 82.9 percent / K2CO3 / aq. ethanol / 18 h / Heating 3: 89.8 percent / H2 / 5percent Pd-C / ethanol 4: 99.3 percent / CH2Cl2 / 1 h / Ambient temperature View Scheme

(heating);

1: zinc; acetic acid / 2.5 h / 55 °C 2: 190 °C 3: trichlorophosphate / 120 °C View Scheme