Reference of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, its 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.
To a solution of methyl 4-amino-2-methoxybenzoate 5 (2.00 g, 11.0 mmol, 1 eq.) in MeCN (70 mL) was added N-iodosuccinimide (5.22 g, 23.2 mmol, 2.1 eq.) in 2 portions over 5 minutes. The resulting mixture was stirred at rt under argon for 1h, then at 55°C. N-iodosuccinimide (1.0 eq.) was added every 5h until completion of the reaction. The reaction mixture was then partitioned between CHCl3 and sat. aq. NaHCO3. A small amount of sat. aq. Na2S2O3 was added to quench potential traces of iodine. The aqueous phase was extracted 3 times. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure. The product (2.10 g, 44percent) was obtained after purification by flash column chromatography (hexane/AcOEt 8:2). Rf 0.4 (hexane/AcOEt, 8:2); 1H NMR (400 MHz, CDCl3) delta 3.85 (s, 3H), 3.88 (s, 3H), 5.15 (br. s., 2H), 8.27 (s, 1H); 13C NMR (100 MHz, CDCl3) delta 52.1, 61.9, 74.0, 81.5, 114.7, 142.4, 151.2, 161.6, 163.7; HRMS (ESI+) m/z calcd for C9H10I2NO3 [M + H]+ 433.8745, found: 433.8746.
Statistics shows that Methyl 4-amino-2-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 27492-84-8.
Reference:
Article; Baud, Matthias G.J.; Bauer, Matthias R.; Verduci, Lorena; Dingler, Felix A.; Patel, Ketan J.; Horil Roy, Deeptee; Joerger, Andreas C.; Fersht, Alan R.; European Journal of Medicinal Chemistry; vol. 152; (2018); p. 101 – 114;,
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