Uses
2-Amino-5-methylbenzonitrile can be used in combination therapy to treat Mucopolysaccharidosis I.
Synthesis
5-Methyl-2-nitrobenzonitrile (1.92 g, 11.84 mmol) was added in batches to a mixed solution of concentrated hydrochloric acid (12 mL) and ethanol (EtOH, 12 mL) with SnCl2 (11.22 g, 59.2 mmol) in stirring. The temperature was controlled at 20-30 °C using an ice bath during the reaction. The reaction mixture was continued to be stirred at room temperature for 1 h. The reaction mixture was then poured into pre-cooled aqueous 6N NaOH solution (ca. 30 mL) and neutralized to pH 7. The product was extracted with ethyl acetate (EtOAc), followed by washing of the organic layer with brine, drying with anhydrous magnesium sulfate (MgSO4), and concentration to give the target product, 2-amino-5-methylbenzonitrile (1.56 g, 99% yield) as a yellowish brown solid. The structure of the product was analyzed by 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 5.79 (bs, 2H), 6.68-6.71 (d, 1H), 7.10-7.13 (dd, 1H), 7.15 (s, 1H); 13C NMR (DMSO-d6) δ 20.13,93.99,116.12, 118.94,125.38,132.32,135.76,150.21; mass spectrum (MS) m/z 133 (MH+) confirmed.
References
[1] Patent: US2008/306053, 2008, A1. Location in patent: Page/Page column 60
[2] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
[3] Patent: US2004/92739, 2004, A1. Location in patent: Page 4
[4] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 2, p. 345 - 349
[5] Chemische Berichte, 1905, vol. 38, p. 3555
