Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, its 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.
General procedure: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.19 (Z)-N-(4-Fluorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-19) Yield 70percent; m.p.: 242-244 °C; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.89 (s, 1H, NNH), 11.33 (s, 1H, NH), 10.84 (s, 1H, SCNH), 7.68-7.66 (m, 2H, J = 8.0 Hz, Ar2-H3 and Ar2-H5), 7.61 (d, 1H J = 7.2 Hz, Ar1-H4), 7.49-7.48 (m, 2H, J = 4.4 Hz, Ar2-H2 and Ar2-H6), 7.20 (d, 1H J = 7.2 Hz, Ar1-H6), 7.03 (t, 1H J = 7.6 Hz, Ar1-H5), 2.24 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.1, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.4, 118.8, 15.8; IR: (KBr, nu/cm-1), 3308 (NN-H), 3165 (CON-H), 3052 (Ar-H), 1695 (-CONH-), 1625 (C=N), 1572 and 1539 (Ar-C=C), 1209 (C=S), 1153 (N-N); Elemental analysis calculated for C16H13FN4OS, C: 58.52, H: 3.99, N: 17.06, found C: 58.75, H: 3.66, N: 17.45.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Zhang, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem