Reference of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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.
To a solution of 4,7-dichloroisatin (0.68 mmol, 1.0 eq) in DMF (4 mL) was added K2CO3 (0.68 mmol, 1.0 eq) at room temperature, the mixture was stirred for about 30 min, and then the propargyl bromide (0.75 mmol, 1.1 eq) was added dropwise. The mixture was stirred overnight at room temperature. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc for several times; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Compound 2, saffron solid, yield: 76%, m. p.: 151.8-153.3 C, Rf = 0.52 (petroleum ether/ethyl acetate 2/1). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J = 8.7 Hz, 1H), 7.10 (d, J = 8.7 Hz, 1H), 4.94 (d, J = 2.4 Hz, 2H), 2.34 (t, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 178.68, 157.00, 146.19, 140.48, 133.05, 126.79, 117.16, 116.11, 77.22, 73.27, 31.94.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.
Reference:
Article; Yu, Bin; Wang, Sai-Qi; Qi, Ping-Ping; Yang, Dong-Xiao; Tang, Kai; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 350 – 360;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem