Synthetic Route of 19798-80-2 , The common heterocyclic compound, 19798-80-2, name is 4-Chloropyridin-2-amine, molecular formula is C5H5ClN2, 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.
N-Iodosuccinimide (9.10 g, 40.4 mmol) was added to a solution of 2-amino-4-chloropyridine 29 (4.00 g, 31.1 mmol) in DMF (40 mL). The reaction mixture was stirred at room temperature for 18 h and partitioned between EtOAc (150 mL) and aqueous sodium thiosulfate solution (1M, 100 mL). The organic fraction was separated, washed successively with water (2 ¡Á 100 mL) and brine (50 mL), dried (MgSO4) and reduced in vacuo to give the crude product as a light orange solid. Column chromatography (SiO2), eluting with 5:1 Petrol-EtOAc to 2:1 Petrol-EtOAc, afforded the title compound16 (4.65 g, 18.4 mmol, 60%) as colourless needles, m.p. 117-120 C (from EtOH-water); Rf 0.57 (1:1 Petrol-EtOAc); (Found: C, 24.1; H, 1.50; N, 11.4; C5H4ClIN2 requires C, 23.6; H, 1.55; N, 11.0%); deltaH (300 MHz, DMSO-d6); 8.21 (1H, s, 6-H), 6.69 (1H, s, 3-H), 6.43 (2H, br s, 2-NH2); deltaC (75 MHz, DMSO-d6); 160.8 (2-C), 156.2 (6-C), 146.3 (4-C), 108.7 (5-C), 79.4 (3-C); numax/cm-1 (solid); 3436, 3284, 3121, 1629 and 1576; m/z (ES) 254.8 (100%, MH+); (Found MH+, 254.9182. C5H4ClIN2 requires MH 254.9180); LC-MS; RT= 1.37min, m/z (ES+) found MH+, 254.8.
The synthetic route of 19798-80-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Yule, Ian A.; Czaplewski, Lloyd G.; Pommier, Stephanie; Davies, David T.; Narramore, Sarah K.; Fishwick, Colin W.G.; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 31 – 38;,
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