Electric Literature of 7251-09-4,Some common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: To an ice-cold suspension of nicotinoyl chloride hydrochloride(I) (1.78 g, 10 mmol) and appropriate 4-aminobenzonitrile (IIa-g) (10 mmol, 1.0 equiv) in acetonitrile(50 ml) under nitrogen was added triethylamine (8.1 g, 11.15 ml,40 mmol, 4.0 equiv) dropwise over 30 min. The resulting suspensionwas stirred at 0 C for 1 h then at room temperatureovernight. The reaction mixture was evaporated, diluted withEtOAc, washed with 10% HCl, brine, dried over anhydrousNa2SO4 and concentrated in vacuo. The resulting solid waswashed with diethyl ether and dried to yield the desired compounds(IIIa-g) in 50-90% yield.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-2-methoxybenzonitrile, its application will become more common.
Reference:
Article; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts