Synthesis
General procedure for the synthesis of 4-amino-3-nitrobenzonitrile from 4'-cyanoacetanilide: potassium nitrate (15.6 mmol) was dissolved in 8 mL of concentrated sulfuric acid and the mixture was cooled to below 0 °C. Under this cooling condition, 7.8 mmol of 4'-cyanoacetanilide was slowly added, keeping the reaction temperature at 0 °C for 3.5 hours. Upon completion of the reaction, the mixture was poured into an ice water bath and the resulting yellow solid was collected by filtration and washed with a small amount of cold water. Subsequently, the resulting product was suspended in 30 mL of 2 mol/L sulfuric acid solution and heated under reflux conditions for 3 hours. At the end of the reaction, the suspension was cooled to room temperature, and the yellow solid was again collected by filtration and washed with a small amount of cold water to finally obtain the target product 4-amino-3-nitrobenzonitrile in 74% yield.
References
[1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 6, p. 1304 - 1317
[2] Journal of the Chemical Society, 1950, p. 1722,1725
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792
[4] Australian Journal of Chemistry, 1994, vol. 47, # 2, p. 247 - 262
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 12, p. 1746 - 1753
