18595-14-7, A common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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 1.0012 g (8.1228 mmol) of pyridine-2-carboxylic acid wasadded 15 mL of thionyl chloride and the reaction mixture wasstirred under reflux for 3 h. Then 1.3425 g (8.1270 mmol) of methyl-4-amino-3-methylbenzoate in 35 mL of chloroformwas added intothe obtained acid chloride. The reactants were stirred under refluxnext 2 h. After chloroform evaporation under vacuum a beigepowder precipitated:(1.5633 g, 5.7839 mmol, yield ca.: 71%, Anal. Calc. C15H14N2O3[%]: C, 66,66; H, 5,22; N, 10,36; Found: C, 66.33; H, 4.90; N, 10.22).The beige crystals occurred after the recrystallization procedurewith the use of 2-propanol. 1H NMR (600 MHz, CDCl3) delta 10.38-10.29 (m, 1H), 8.66-8.62 (m, 1H), 8.53 (d, J 8.5 Hz, 1H),8.31 (d, J 7.8 Hz, 1H), 7.98-7.95 (m, J 8.6 Hz, 1H), 7.95-7.90 (m,J 3.4 Hz, 1H), 7.51 (td, J 7.3, 4.9 Hz, 1H), 3.91 (s, 1H), 2.47 (s, 1H).13C NMR (151 MHz, CDCl3) delta 167.22, 162.35, 150.11, 148.53, 140.62,138.15, 132.11, 129.18, 127.13, 127.07, 125.77, 122.87, 120.01, 77.58,77.37, 77.16, 52.32, 17.96. FT-IR (KBr, cm-1): 3435 n(O-H KBr), 3342n(N-H), 3098, 3062, 2997, 2951, 2905, 2839 n(C-H), 1712, 1698n(C]O), 1609-1440 n(ringC]C), 1292-1095 n(C-O) and (C-N)overlapped, 769, 684, 622 d(C-H ringC]C)oop.
The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Skokowski, Przemys?aw; Gruszczy?ska, Joanna; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1178; (2019); p. 669 – 681;,
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