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. Quality Control of Indolin-2-one
An oven-dried 250 mL round-bottom flask containing indolin-2-one (5.00 g, 36.7 mmol) was fitted with a stirbar and septa, then flushed with nitrogen. Tetrahydrofuran (50 mL) was added and the mixture cooled to -78 . A solution of n-butyllithium in hexane (32.3 mL, 80.7 mmol, 2.5 M solution) was added, and the resulting solution was stirred at -78 for 30 minutes. Next, iodomethane (13.0 g, 91.8 mmol) was added and the mixture stirred at -78 for 10 minutes. The reaction solution was quenched with saturated aqueous ammonia hydrochloride solution. The resulting mixture was extracted with EtOAc (3 x 30 mL) and the combined organic layers were washed with brine (50 mL) , dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on SiO2(0to 50EtOAc/petroleum ether) to afford 3-methylindolin-2-one. MS (EI) calc?d for C9H10NO [M+H]+, 148 found, 148.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem