Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 5446-92-4, name is 2-Methoxy-5-nitropyridine. A new synthetic method of this compound is introduced below., 5446-92-4
General procedure: A stirred mixture of nitroarene 1 (1 mmol), allyl sulfone 2 (1.1 mmol), MgCl2 (60 mg, 0.62 mmol), and bis-trimethylsilylacetamide (BSA, 0.51 g, 0.64 mL, 2.5 mmol) in HMPA (2 mL) was treated with DBU (0.76 g, 0.75 mL 5.0 mmol). Stirring was continued for 2 days. After completion (disappearing of the nitroarene, TLC control), the reaction mixture was poured into saturated aqueous NH4Cl and extracted with ethyl acetate (3¡Á25 mL). After drying with MgSO4 and removal of the solvent the crude product was chromatographed Colorless crystals; mp 173-176 C (hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) delta 1.50 (s, 9H), 2.40 (s, 3H), 3.96 (s, 3H), 7.06 (d, J=8.5 Hz, 1H), 7.26-7.29 (m, 2H), 7.98 (d, J=7.5 Hz, 2H), 8.16 (d, J=9.0 Hz, 1H), 8.51 (s, 1H); 13C NMR (100 MHz, CDCl3) delta 21.62, 30.13, 38.45, 54.69, 117.13, 120.36, 128.50, 129.18, 135.14, 138.14, 140.20, 142.27, 142.91, 144.23, 162.13, 167.12; numax (film from CH2Cl2) 2886, 1679, 1460, 1296, 1201, 1150, 1067, 984, 746 cm-1; EIMS (70 eV) m/z (% relative intensity): 355 (29), 307 (16), 306 (54), 305 (100), 292 (15), 291 (44), 275 (17), 264 (19), 249 (37), 138 (15), 91 (16); HRMS (EI) for C20H22N2O3S calcd 370.1351; found 370.1347.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,5446-92-4, 2-Methoxy-5-nitropyridine, and friends who are interested can also refer to it.
Reference:
Article; Anczkiewicz, Karolina; Krolikiewicz, Magdalena; Wrobel, Zbigniew; Wojciechowski, Krzysztof; Tetrahedron; vol. 71; 23; (2015); p. 3924 – 3931;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem