hydrogen; palladium on activated charcoal in ethyl acetate

potassium hydroxide; hydrazine hydrate in ethylene glycol T=170 - 175°C; 8 h;

potassium tert-butylate in xylene T=150°C; 12 h;

Wolff-Kishner reduction

1: 85 percent / HCl / 1.5 h / Heating 2: 63 percent / BCl3 / CH2Cl2 / 0.17 h / Ambient temperature 3: 81 percent / conc.HCl, H2 / platinum oxide / methanol 4: 82.5 percent / K2CO3 / dimethylformamide / 4 h / 80 °C 5: 92 percent / NaOH / H2O; methanol / 3 h / Heating 6: 77.5 percent / diethyl ether / 4 h / Ambient temperature 7: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme

1: 63 percent / BCl3 / CH2Cl2 / 0.17 h / Ambient temperature 2: 81 percent / conc.HCl, H2 / platinum oxide / methanol 3: 82.5 percent / K2CO3 / dimethylformamide / 4 h / 80 °C 4: 92 percent / NaOH / H2O; methanol / 3 h / Heating 5: 77.5 percent / diethyl ether / 4 h / Ambient temperature 6: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme

1: 82.5 percent / K2CO3 / dimethylformamide / 4 h / 80 °C 2: 92 percent / NaOH / H2O; methanol / 3 h / Heating 3: 77.5 percent / diethyl ether / 4 h / Ambient temperature 4: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme

1: 81 percent / conc.HCl, H2 / platinum oxide / methanol 2: 82.5 percent / K2CO3 / dimethylformamide / 4 h / 80 °C 3: 92 percent / NaOH / H2O; methanol / 3 h / Heating 4: 77.5 percent / diethyl ether / 4 h / Ambient temperature 5: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme

1: 77.5 percent / diethyl ether / 4 h / Ambient temperature 2: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme

1: 92 percent / NaOH / H2O; methanol / 3 h / Heating 2: 77.5 percent / diethyl ether / 4 h / Ambient temperature 3: 91.5 percent / H2 / Pd-C / ethyl acetate View Scheme