Synthesis
Part A. Synthesis of 4-cyanobenzoic acid hydrazide
A mixture of methyl 4-cyanobenzoate (10.8 g, 67 mmol) and hydrazine monohydrate (18.6 g, 371 mmol) in anhydrous ethanol (70 mL) was heated to reflux for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature. The solid product formed was collected by filtration and washed with cold ethanol (20 mL). Subsequently, the product was dried to give 4-cyanobenzoylhydrazine (8.7 g, 81% yield). The melting point of the product was 201 °C. 1H NMR (300 MHz, CDCl3) δ 4.14 (s, 2H), 7.40 (s, 1H), 7.76 (d, J = 8 Hz, 2H), 7.88 (d, J = 8 Hz, 2H); MS (NH3-Cl) calculated value (M + 1)+: 162, measured value: 162.
References
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