Synthetic Route of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. A new synthetic method of this compound is introduced below.
A three-neck, 3L round bottomed flask fitted with a mechanical stirrer and a reflux condersor was charged with 4-aminophenol (41.35 g, 0.38 mol) and N5N- dimethylacetamide (500 mL). The resulting solution was degassed with bubbling nitrogen before potassium tert-butoxide was added portionwise (44.54 g, 0.40 mol). The solution became green at first, then became an off-white suspension, to which was added 4- chloropyridine-2-carbonitrile (50.00 g, 0.36 mol) in N,N-dimethylacetamide (300 mL) in one portion. The mixture turned brown within minutes and it was heated to 900C overnight. In the next morning, the mixture was cooled to rt and the solvent was removed under vacuum. The resulting residue was partitioned between water (1.5 L) and EtOAc (1.5 L). K2CO3 was added to adjust the pH to slightly basic and the layers were separated. The aqueous layer was extracted with EtOAc (IL). The combined organic phase was dried over MgSO4, filtered and concentrated. The resulting residue was dissolved in dichloromethane and absorbed onto a plug of silica gel (~ 1 kg). It was then eluted with 25% to 75% EtOAc in hexanes to afford 4-(4-aminophenoxy)pyridine-2-carbonitrile (18.9 g, 25%): 1H NMR (DMSO-^5) delta ppm 8.48 (d, IH), 7.51 (d, IH), 7.04 (dd, IH), 6.83 (dd, 2H), 6.60 (dd, 2H), 5.18 (s, 2H); MS ES 212 (M+H), RT 0.97 min.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,19235-89-3, 4-Chloropyridine-2-carbonitrile, and friends who are interested can also refer to it.
Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/110763; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem