In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20870-79-5 as follows. Application In Synthesis of 5-Nitroindolin-2-one
To a suspension of the lactam (10.0 g, 56 mmol) in 200 ml of 1 ,2-dichloroethane, was added POBr3 (15.3g, 53.2 mmol) at RT. The resulting mixture was heated at reflux temperature in a 9OC oil bath for 0.5 hour (the reaction formed a copious amount of precipitate, and an oil bath was preferred over a heating mantle, as it provided gentle heating and avoided a darkening of the precipitate). The reaction was cooled just below reflux temperature, and imidazole (4.57 g, 62 mmol) was added in one portion. The resulting gummy suspension was heated at reflux temperature in an oil bath for another 2 hours. The reaction was cooled to RT, and 100 mL of ice-water was added. Solid NaHCO3 (ca. 50 g) was added to the mixture until no further gas was evolved. The suspension was extracted with DCM (4chi), and the combined DCM extracts were washed with 300 mL of brine. The DCM extracts were filtered through silica gel and concentrated to dryness to afford a crude product. The crude product was recrystallized from chloroform to give 5.41 g of the desired compound as a white solid. The filtrate was concentrated to dryness, and the residue was purified by flash column chromatography (30% EtO Ac/Hex) to give an additional 2.6 g of desired product. MS (ESI) m/e (MH-H+): 242.
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Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); A1;,
Indoline – Wikipedia,
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