Uses
ETHYL 5-AMINO-1-METHYLPYRAZOLE-4-CARBOXYLATE features an amino group and a carboxylic acid moiety, which contribute to its reactivity and potential applications in various chemical reactions. The ethyl ester functional group enhances its solubility in organic solvents, making it useful in synthetic chemistry.
Synthesis
Example A Synthesis of ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate: methylhydrazine (8.6 mL, 162 mmol) was slowly added to a solution of ethyl (ethoxymethylene)cyanoacetate (24.9 g, 147 mmol) in ethanol (250 mL). The reaction mixture was heated to reflux and stirred continuously for 3 days. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by recrystallization from a mixed ethyl acetate/petroleum ether solvent to afford a white solid product identified as ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate (21.1 g, 85% yield).
References
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8670 - 8692
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4585 - 4589
[3] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 749 - 755
[4] Patent: EP1512687, 2005, A1. Location in patent: Page/Page column 6
[5] Patent: US5498630, 1996, A
