Application of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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.
An oven-dried screw cap test tube was charged with a magnetic stir bar, 5-nitroisatin (1; 0.192 g, 1 mmol), malononitrile (2; 0.073 g,1.1 mmol), trisodium citrate dihydrate (0.029 g, 10 mol % as organo catalyst),and EtOH:H2O (1:1 v/v; 4 mL) in a sequential manner; the reaction mixture was then stirred vigorously at room temperature for about 20 min. After that, ethyl acetoacetate (3; 0.130 g, 1 mmol)was added to the stirred reaction mixture, and the stirring was continued for 3 h [15]. The progress of the reaction was monitoredby TLC. On completion of the reaction, a solid mass precipitated out that was filtered off followed by washing with aqueous ethanol to obtain crude product. It was purified just by recrystallization from ethanol without carrying out column chromatography. The structure of ethyl 2′-amino-3′-cyano-6′-methyl-5-nitro-2-oxospiro[indoline-3,4′-pyran]-5′-carboxylate (4) was confirmed by analytical as well as spectral studies including FT-IR, 1H NMR, 13C NMR,and TOF-MS.
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-2,3-dione, its application will become more common.
Reference:
Article; Sharma, Sakshi; Brahmachari, Goutam; Banerjee, Bubun; Nurjamal, Khondekar; Kumar, Abhishek; Srivastava, Ambrish Kumar; Misra, Neeraj; Pandey, Sarvesh Kumar; Rajnikant; Gupta, Vivek K.; Journal of Molecular Structure; vol. 1118; (2016); p. 344 – 355;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem