3-Amino-4-methylbenzonitrile

Chemical Properties

off-white crystalline

Uses

3-Amino-4-methylbenzonitrile is an organic compound commonly used as an intermediate in organic synthesis, especially in pharmaceutical and pesticide chemistry.

Synthesis

C.14.b. Synthesis of 3-amino-4-methylbenzonitrile: 120 g of 3-nitro-4-methylbenzonitrile was suspended in 1.2 L of ethanol, and 7 g of 10% Pd/C catalyst was added and the hydrogenation reaction was carried out in a 50 L hydrogen atmosphere at room temperature. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration, followed by distillation under reduced pressure to remove the solvent to afford 95 g of pure 3-amino-4-methylbenzonitrile in 97% yield. The product was characterized by 1H-NMR (DMSO-d6; δ, ppm): 7.1 (dd, 1H); 6.90 (d, 1H); 6.85 (d, 1H); 5.35 (s, 2H, NH2); 2.15 (s, 3H).

References

[1] Patent: US6455671, 2002, B1
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1203 - 1208
[3] Chemische Berichte, 1903, vol. 36, p. 4359
[4] Chemische Berichte, 1904, vol. 37, p. 1845
[5] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1997, vol. 53, # 2, p. 141 - 150