With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-75-7,3-Oxo-3,4-dihydroquinoxaline-2-carboxylic acid,as a common compound, the synthetic route is as follows.
A solution of 3-hydroxyquinoxaline-2-carboxylic acid, 9(500 mg, 2.63 mmol), and amino nitrile 6 (406 mg, 2.63 mmol) in anhydrous DMF (36 mL) was cooled down to 0Cin an ice/NaCl bath. To the cold solution, EDC¡¤HCl (1.50 g,7.89 mmol) and HOBt (1.46 g, 10.8 mmol) were added portionwiseover 30 min. The reaction mixture was stirred atroom temperature overnight and concentrated under vacuum.The resulting residue was taken CH2Cl2 (50 mL), treatedwith 2N NaOH until pH 14, and extracted with CH2Cl2 (3 ¡Á50 mL). The aqueous layer was treated with 1N HCl until pH1, extracted with CH2Cl2 (3 ¡Á 50 mL), and washed with brine(2 ¡Á 50 mL). The combined organic extracts were dried overanhydrous Na2SO4, concentrated under reduced pressure andthe resulting solid residue was washed with pentane (3 ¡Á 20mL), to provide amido nitrile 10 (730 mg, 85% yield) as ayellow solid; mp 181-182C; IR (ATR) nu 3081 (O-H, N-Hst), 2241 (CN st), 1678 (C=O st); 1H NMR (400 MHz,CD3OD) delta 1.41-1.50 (m, 8H), 1.61-1.71 (m, 4H), 2.43 (t, J =7.2 Hz, 2H), 3.48 (t, J = 7.2 Hz, 2H), 7.38 (dd, J = 8.4 Hz,J? = 1.2 Hz, 1H), 7.43 (ddd, J = 8.4 Hz, J? = 7.2 Hz, J? = 1.2Hz, 1H), 7.67 (ddd, J = 8.4 Hz, J? = 7.2 Hz, J? = 1.2 Hz,1H), 7.98 (dd, J = 8.4 Hz, J? = 1.2 Hz, 1H); 13C NMR (100.6MHz, DMSO-d6) delta 16.1, 24.7, 26.3, 28.0, 28.1, 28.5, 28.9,38.7, 115.57, 115.60, 120.7, 123.8, 129.2, 131.2, 131.7,132.4, 153.9, 163.0; HRMS (ESI), calcd for (C18H22N4O2 +H+) 327.1816, found 327.1817., 1204-75-7
As the paragraph descriping shows that 1204-75-7 is playing an increasingly important role.
Reference£º
Article; Artigas, Albert; Sola, Irene; Taylor, Martin C.; Clos, M. Victoria; Perez, Belen; Kelly, John M.; Munoz-Torrero, Diego; Letters in Organic Chemistry; vol. 15; 5; (2018); p. 455 – 461;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider