Application of 112656-95-8,Some common heterocyclic compound, 112656-95-8, name is 7-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.
The solution of 7-nitro-isatin (15) (3 g, 0.016 mol), cyanoacetic acid (1.33 g, 0.016 mol) and piperidine (0.10 ml) in pyridine (15 ml) was refluxed for 30 hours. After cooling to room temperature, concentrated hydrochloric acid (1 ml) and water (10 ml) were added. The product was obtained by extraction with ethylacetate. Organics were dried under sodium sulfate, solvent was removed in vacuum to give 2 g (60 % yield) of (7-nitro-2-oxindole-3-yliden)acetonitrile. mp (exp.) = 224-225 0C. Spectrum NMR 1 (DMSO-d6, delta, ppm, J, Hz): 6.94 (s, 1H), 7.28 (dd, J = 7.45; J = 8.34, 1H); 7.86 (d, J = 7.20, 1H), 8.10 (d, J = 8.59, 1H), 11.33 (s, 1H). Spectrum NMR 13C (DMSO-d6, delta, ppm): 70.99; 117.17; 122.89; 125.25; 130.77; 131.62; 133.82; 138.63; 177.50. IR spectrum (sm-1): 1535; 1598; 1626 (NO2), 1727 (C=O), 2926; 2958 (C=C-H), 3239; 3348 (NH). MS (EI, 70 eV), m/z (I, %): 233 (77, [M*H2O]+), 215 (26, M+), 193 (86), 189 (44), 175 (50), 149 (32), 145 (60), 118 (70), 90 (31), 63 (31), 41 (40), 30 (100).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Nitroindoline-2,3-dione, its application will become more common.
Reference:
Article; Zaryanova, Ekaterina V.; Lozinskaya, Nataly A.; Beznos, Olga V.; Volkova, Maria S.; Chesnokova, Nataly B.; Zefirov, Nikolay S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3787 – 3793;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem