Synthesis
GENERAL METHOD: p-Methylphenylhydrazine (0.001 mol) was mixed with 10 mL of ethanol, stirred and heated to reflux. Subsequently, ethoxymethylene malononitrile (0.001 mol) dissolved in 10 mL of ethanol was added slowly and dropwise. The reaction mixture was kept at reflux for 2 hours. After completion of the reaction, the mixture was poured into 50 mL of ice water. The precipitated solid product was collected by filtration and washed with cold water to give the final 5-amino-1-toluene-1H-pyrazole-4-carbonitrile in 61-80% yield.
References
[1] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1876 - 1884
[2] Heterocyclic Communications, 2005, vol. 11, # 5, p. 385 - 388
[3] European Journal of Medicinal Chemistry, 2008, vol. 43, # 4, p. 771 - 780
[4] Journal of Organic Chemistry, 1956, vol. 21, p. 1240,1242
[5] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2121 - 2125
