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. 502509-10-6, name is 4-(2-Hydroxyethyl)picolinic acid. A new synthetic method of this compound is introduced below., Formula: C8H9NO3
To a stirred solution of acid 70 (4.76 g, 23.4 mmol) acid in MeOH (104 mL) at 0 C was slowly added thionyl chloride (3.40 mL, 46.8 mmol) and was heated at reflux during 24 h. After cooling at 0 C, thionyl chloride (3.40 mL, 46.8 mmol) was added in second time and heated at reflux during 24 h. Then, the mixture was concentrated in vacuo and a saturated aqueous solution of NaHCO3 was added until basic pH. The aqueous layer was extracted with EtOAc (thrice). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 36 as black oil in 38% yield (1.60 g). The crude product was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) delta 8.43 (d, J = 4.9 Hz, 1H), 7.90 (d, J = 0.9 Hz, 1H), 7.27 (dd, J = 5.0, 1.7 Hz, 1H), 3.88 (s, 3H), 3.84 (t, J = 6.4 Hz, 2H), 3.44 (bs, 1H), 2.83 (t, J = 6.3 Hz, 2H). 13C NMR (75 MHz, CDCl3) delta 165.6, 150.2, 149.3, 147.3, 127.8, 125.8, 61.7, 52.7, 38.2. MS (ESI+): m/z (%): 182 (100) [M+H]+.
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Reference:
Article; Oukoloff, Killian; Coquelle, Nicolas; Bartolini, Manuela; Naldi, Marina; Le Guevel, Remy; Bach, Stephane; Josselin, Beatrice; Ruchaud, Sandrine; Catto, Marco; Pisani, Leonardo; Denora, Nunzio; Iacobazzi, Rosa Maria; Silman, Israel; Sussman, Joel L.; Buron, Frederic; Colletier, Jacques-Philippe; Jean, Ludovic; Routier, Sylvain; Renard, Pierre-Yves; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 58 – 77;,
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