Reference of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent. Spiro[cyclopropane-1,3?-indoline]-2?-one (10a). Colorless crystalline (24 mg, 75 % yield). mp 177 – 180 C. Analytical data for 10a was consistent with that previously reported [10h]. 1H NMR (300 MHz, CDCl3): delta 8.94 (s, 1H), 7.16 – 7.26 (m, 1H), 6.97 – 7.00 (m, 2H), 6.84 (d, J=7.4Hz, 1H), 1.75 – 1.79 (m, 2H), 1.52 – 1.56 (m, 2H); delta13C NMR (75 MHz, CDCl3): delta 179.8, 140.8, 131.3, 126.8, 122.0, 118.6, 109.9, 27.6, 19.5. HRMS (ESI-TOF) calcd for C10H10NO [M+H] +: 160.0757; found: 160.0757.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-2-one, its application will become more common.
Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem