Synthetic Route of 59782-86-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.59782-86-4, name is 2-Chloro-5-iodonicotinic acid, molecular formula is C6H3ClINO2, molecular weight is 283.45, as common compound, the synthetic route is as follows.
The mixture of 19 (29.8 g, 107 mmol), DMF (1.5 mL) and SOCl2 (78 mL, 10 eq.) was stirred at 70 C for 4 h. The mixture was concentrated in vacuo and diluted with DMF (6 mL). Water (90 mL) was slowly added to the mixture and then satd NaHCO3 aq (200 mL) was slowly added. The mixture was acidified to pH 4 by 1 N HCl (55 mL) and stirred at room temperature for 2 h and at 0 C overnight. After filtration, the solid was washed with water and dried in vacuo to yield a crude mixture of 2-chloro-5-iodonicotinic acid as a pale yellow solid (27 g). The solid was suspended in CHCl3 (135 mL) and SOCl2 (13.9 mL) and the suspension was stirred at reflux for 0.5 h. DMF (0.5 mL) and SOCl2 (27.8 mL) were added to make a clear solution and the mixture was stirred at reflux for 1.5 h, then cooled and concentrated in vacuo. EtOH (135 mL) was slowly added to the residue at 0 C and the mixture was stirred at 0 C for 15 min. and at room temperature for 30 min. The mixture was concentrated in vacuo and partitioned between AcOEt (270 mL) and satd NaHCO3 aq (135 mL). The aqueous phase was extracted with AcOEt (135 mL) and the combined organic phase was washed with brine, dried over Na2SO4 and filtered. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (AcOEt/n-hexane; 0:100 to 20:80) to yield 20 as a white solid (27.25 g, 95%). 1H NMR (400 MHz, CDCl3) delta = 8.70 (d, J = 2.0 Hz, 1H), 8.41 (d, J = 2.0 Hz, 1H), 4.42 (q, J = 7.2 Hz, 2H), 1.42 (t, J = 7.2 Hz, 3H); MS (ESI+) 311.9 (M+H)+.
The chemical industry reduces the impact on the environment during synthesis 59782-86-4, I believe this compound will play a more active role in future production and life.
Reference:
Article; Takahashi, Bitoku; Funami, Hideaki; Iwaki, Takehiko; Maruoka, Hiroshi; Shibata, Makoto; Koyama, Makoto; Nagahira, Asako; Kamiide, Yoshiyuki; Kanki, Satomi; Igawa, Yoshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4792 – 4803;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem