Uses
5-Amino-2-methylbenzonitrile may be used as a starting material for the synthesis of 5-iodo-2-methylbenzonitrile and 5-hydroxy-2-methylbenzonitrile. It may also be used in the preparation of 5-(2,4-dioxothiazolidin-3-yl)-2-methylbenzonitrile by reacting with thioglycolic acid methyl ester in the presence of 1,1′-carbonyldiimidazole.
Synthesis
Step 2: Synthesis of 5-amino-2-methylbenzonitrile: 2-methyl-5-nitrobenzonitrile (25.0 g, 154 mmol), 10% palladium carbon catalyst (2.5 g), ethyl acetate (150 mL) and ethanol (150 mL) were mixed. The reaction mixture was stirred under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a pad of diatomaceous earth followed by concentration of the filtrate to afford 5-amino-2-methylbenzenecarbonitrile (19.6 g, 96% yield), the product was a tan solid. Mass spectral analysis showed m/e = 133 (M + H). Reference: Scholz, D. et al, J. Med. Chem. 41, 1050-1059 (1998).
References
[1] Patent: WO2005/97750, 2005, A1. Location in patent: Page/Page column 69
[2] Organic Letters, 2017, vol. 19, # 18, p. 4746 - 4749
[3] Organic Letters, 2003, vol. 5, # 7, p. 1131 - 1134
[4] Journal of Materials Chemistry, 2011, vol. 21, # 26, p. 9523 - 9531
[5] Patent: US5596006, 1997, A
