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.
A mixture of silver sulfate (100 g, 0. 32 mol) and iodine (82 g, 0.32 mol) IN NN-DIMETHYLFORMAMIDE (700 mL) and ethanol (1400 mL) was treated with 5-nitro-2, 3-DIHYDRO-1H-INDOLE I (48 G, 0. 29 mol). The resulting mixture was stirred at 25C for 1.5 h, filtered and the filter pad washed with ethyl acetate. The filtrate was concentrated in vacuo to a volume of approximately 500 mL. This solution was treated with a L. oN aqueous sodium thiosulfate solution (100 mL) and a saturated aqueous sodium chloride solution (400 mL). The resulting precipitate was collected by filtration, washed with water and petroleum ether, and dried in vacuo to afford 7-IODO-5-NITRO-2, 3-DIHYDRO-1H-INDOLE II (83.9 G, 98. 9%) as a white solid: 1H NMR (DMSO-D6, 300 MHz) 8 8. 18 (d, J = 2. 20 Hz, 1H), 7. 80 (d, J = 1. 46 Hz, 1H), 7. 03 (broad s, 1H), 3.65 (t, J = 8. 97 Hz, 2H), 3. 17 (t, J = 8. 60 Hz, 2H).
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:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/101568; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem