Category: 5446-92-4

5446-92-4, 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.

[0238] A mixture of 2-methoxy-5-nitropyridine (5.0 g,32.4 mmol) in HOAc (50 ml) was added iron powder (5 g,89.53 mmol). After the mixture was heated to 60 C. for 2 h,the mixture was filtered through celite, and the filtered cakewas washed with HOAc and then water. The filtrate wasconcentrate and the residue was neutralized with saturatedNaHC03 solution, the aqueous phase was extracted withDCM (1 00 ml), and insoluble materials were removed byfiltration. After the aqueous phase was extracted with DCM(100 mlx4), the combined organic phase was washed withbrine and concentrated to afford crude product, which waspurified by silica gel colunm chromatography (2% MeOH inDCM) to afford compound 22 (3.5 g, yield 86%) as a brownoil[0239] m/z: [M+Ht 125.2

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:
Patent; Gao, Daxin; Yang, Heping; Yu, Yajun; US2014/329800; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

5446-92-4 , The common heterocyclic compound, 5446-92-4, name is 2-Methoxy-5-nitropyridine, molecular formula is C6H6N2O3, 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.

Preparation of 5-Methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (Formula 10); 2-Methoxy-5-nitro-pyridine (Formula 6, 4 g, 25.6 mmole) and 4-chlorophenoxyacetonitrile (Formula 7, 4.8 g, 28.5 mmole) were dissolved in THF (58 mL). The resulting solution was slowly added to a solution of t-BuOK (6.3 g, 56.3 mmole) in THF dry (60 mL) at -10 C. The reaction mixture was stirred for 3 h at -10 C., and then water was added. The aqueous layer was extracted with EtOAc. The combined organic layers were dried on Na2SO4 and evaporated to give a crude that was purified by silica gel column chromatography (eluent: petroleum ether/EtOAc 8:2) to give (6-methoxy-3-nitro-pyridin-2-yl)-acetonitrile (Formula 8, Yield: 50%. MS (m/z): 194.1 (MH+)).To a solution of (6-methoxy-3-nitro-pyridin-2-yl)-acetonitrile (Formula 8, 1 g, 5.18 mmole) in EtOH (30 mL), 10% Pd/C was added. The mixture was hydrogenated at 45 psi at room temperature overnight. The catalyst was filtered off and the solvent was evaporated. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/EtOAc 8:2) to give 5-methoxy-1H-pyrrolo[3,2-b]pyridine (Formula 9, Yield: 64%. MS (m/z): 149 (MH+).To a solution of 5-methoxy-1H-pyrrolo[3,2-b]pyridine (Formula 9, 498 mg, 3.36 mmole) in 33% acetic acid (5.2 mL), hexamethylenetetramine (714 mg, 5.05 mmole) was added. The reaction mixture was refluxed for 4 hours. After cooling, the reaction was extracted with EtOAc. The combined organic layers were dried on Na2SO4 and evaporated to give a crude that was purified twice by silica gel column chromatography (eluent: methylene chloride/MeOH 95:5) to give 5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (Formula 10, Yield: 27%. MS (m/z): 177.17 (MH+)).

According to the analysis of related databases, 5446-92-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/298820; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem