Reference of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.
1-Acetyl-2-formyl-3-hydroxyindole (XIII) [1]. 198 ml (?1.24 mol) of DMF diethyl acetal is added into a suspension of 56 g (0,32 mol) indoxyl XI in 640 ml of benzene and stirred for 1 hour at 20C. The resulting solution is refluxed for 1 hour. Benzene is evaporated in vacuo, with bath temperature less than 60C. After evaporating benzene, the residue is dissolved in ? 4 liters of water and acidified (pH 2-3) by 60 ml of conc. HCl. After 5 min the solid is filtered and washed with water and isopropyl alcohol. 45.5 g (yield 70%) of compound XIII is obtained. Melting point 122-123C (from isopropyl alcohol). IRS, v, cm-1: 1700, 1620, 1580. MS: M+ 203. Founs, % : C 64.73, H 4.50, N 6.90. C11H9NO3. Calc., %: C 65.02, H 4.47, N 6.89. 1H NMR (CDCl3, delta, ppm): 10.24 (1H, br.s, CHO); 2.79 (3H, s, NCOCH3); 7.34-7.91 (4H, m, Ar). UV-Vis, lambdamax, nm (lg epsilon): 230 (4.22), 257 (4.03), 312 (3.95), 356 HM (3.89).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Acetylindolin-3-one, its application will become more common.
Reference:
Patent; Proton OOO; GRANIK, Vladimir Grigorievich; RYABOVA, Svetlana Yurevna; PARSHIN, Valery Aleksandrovich; ALEKSEEVA, Ludmila Mikhaylovna; GRIGORIEV, Nikita Borisovich; EP2738167; (2014); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem