Application of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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: Methyl 4-amino-3-methylbenzoate (6) (10.00g, 60.58mmol) was acylated with alkyl acyl chloride (90.87mmol) and triethylamine (16.79mL, 121.16mmol) in DCM at 0C. The resulting amide was reacted with fuming nitric acid in sulfuric acid (60%) at-20C. The resulting nitro-compound was reduced with hydrogen (5bar) and Raney Ni (0.79g, 13.34mmol) in methanol at 100C. The resulting amino compound was dissolved in glacial acetic acid and heated under reflux for 1h. After evaporation of the acetic acid, water was added and the pH was adjusted to 9 by addition of concentrated ammonia. This solution was extracted with ethyl acetate (3×100mL). The combined organic layers were washed with aqueous NaHCO3 solution and dried over MgSO4. After filtration, the solvent was removed under reduced pressure.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-methylbenzoate, its application will become more common.
Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
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