Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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.
We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid. Mp: 177.0-178.1 C. 1H NMR (400 MHz, DMSO-d6): delta = 8.00 (1H, m), 7.86 (1H, s), 7.26 (4H, m), 6.70 (1H, d, J = 8.94 Hz), 5.71 (1H, s), 3.81 (1H, m), 3.21 (1H, m), 3.00 (2H, m), 2.32 (3H, s); 13C NMR (400 MHz, DMSO-d6): delta = 171.16, 156.59, 137.70, 137.38, 131.42, 130.49, 129.23, 128.83, 126.02, 120.28, 104.61, 61.16, 49.18, 26.15, 20.68 ppm. Calculated for C17H16N2O4, MS (ESI): m/z = 313.1181 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline, its application will become more common.
Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem