Uses
2-Amino-1-cyclopentene-1-carbonitrile s an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.
Synthesis
General procedure for the synthesis of 2-amino-1-cyclopentene-1-carbonitrile from hexanedinitrile: hexanedinitrile (5.40 g, 50 mmol) was mixed with powdered potassium tert-butanolate (t-BuOK, 6.72 g, 60 mmol) and the reaction was stirred at room temperature overnight. Upon completion of the reaction, water was added to the reaction mixture, and the precipitated crystalline solid was collected by filtration and purified by recrystallization with methanol (MeOH) to finally obtain the target product 2-amino-1-cyclopentene-1-carbonitrile (4.26 g, 79% yield).
References
[1] Synthetic Communications, 1984, vol. 14, # 10, p. 967 - 972
[2] Tetrahedron Asymmetry, 2011, vol. 22, # 5, p. 506 - 511
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 625 - 629
[4] Journal of the American Chemical Society, 1987, vol. 109, p. 1160
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 371 - 376