Electric Literature of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.
To a mixture of 5-nitroindolin-2-one (15 g, 84 mol)in 1,2-dichioroethane (300 mL) was added POBr3 (23 g,80 mmol) . The mixture was heated to 90C and stirred for0.5 h. Then the reaction was cooled just below 90C andimidazole (6.9 g, 101 mmcl) was added in one portion. The mixture was stirred at 90C for 2 h. The reaction was quenched by ice water (200 mL) and then extracted with DCM (200 mL x 3) . The combined organic phase was washed with brine (300 mL x 2), dried over anhydrousNa2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10:1 to 5:1 to 3:1) to give the title compound (11 g, 46 mmol, 54%yield) as a solid.H NMR (400 MHz, DMSO-d6) oe (ppm) 6.86 (s, 1H), 7.49 (d,J=9.2 Hz, 1H) , 7.91 – 8.07 (m, 1H) , 8.50 (s, 1H) , 12.63(br 5, 1H)
The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; NAKAMURA, Tsuyoshi; AKIU, Mayuko; TSUJI, Takashi; TANAKA, Jun; TERAYAMA, Koji; YOKOYAMA, Mika; PINKERTON, Anthony, B.; SESSIONS, Edward, Hampton; (289 pag.)WO2020/10252; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem