GENERAL STEPS: In a typical reaction, 5.0 mg of Pd-gCN catalyst (containing 5.0 wt% Pd) was mixed with 1.0 mM 1-(4-nitrophenyl)-1H-pyrazole in ethanol (2 mL) and 60% hydrazine hydrate solution (2 mM, 1.2 equiv, 0.07 mL). The mixture was placed in a 10 mL round-bottomed flask and reacted at reflux temperature (70°C) for 4 hours, followed by cooling to room temperature. After completion of the reaction, the reaction mixture was filtered and the filtrate was purified by silica gel column chromatography to afford 4-(1H-pyrazol-1-yl)aniline (1-(4-aminophenyl)pyrazole). For dinitroaromatic substrates, 4.0 mM (2.4 eq., 0.14 mL) of 60% hydrazine hydrate solution is required.
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