Research on new synthetic routes about 7-Nitroindoline-2,3-dione

The chemical industry reduces the impact on the environment during synthesis 7-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Application of 112656-95-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 112656-95-8, name is 7-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

The solution of 7-nitroisatin (15) (3 g, 0.016 mol), malonic acid (1.63 g, 0.016 mol) and piperidine (0.10 ml) in pyridine (10 ml) was refluxed for 20 hours. After cooling to room temperature, the solution of hydrochloric acid in 1,4-dioxane (16 %, 1 ml) was added. The solvent was evaporated in vacuum. The solid was washed with concentrated hydrochloric acid, the precipitate was collected by vacuum filtration, washed with small amount aqueous hydrochloric acid and water, dried on air to give 0.84 g (21 % yield) of (7-nitro-3-hydroxy-2-oxindole-3-yl)acetic acid. mp (exp.) = 242-243 0C. Spectrum NMR 1 (DMSO-d6, delta, ppm, J, Hz): 3.02 (d, J = 16.51, 1H), 3.12 (d, J = 16.51, 1H), 7.15 (dd, J = 7.09, J = 8.56, 1H); 7.75 (d, J = 6.97, 1H), 8.00 (dd, J = 1.10, J = 8.56, 1H), 11.06 (s, 1H). Spectrum NMR 13C (DMSO-d6, delta, ppm): 41,78; 71,41; 122,23; 124,39; 130,47; 131,10; 135,71; 140,04; 170,75; 178,94. IR spectrum (sm-1): 1470 (CH2), 1534; 1630 (NO2), 1698 (C=O), 1720 (C=O), 3227 (NH), 3447 (OH), 3000-3500 (OH). MS (EI, 70 eV), m/z (I, %): 252 (54, M+), 234 (46), 190 (85), 175 (76), 145 (100), 118 (46), 104 (32), 63 (26), 45 (55), 30 (55).

The chemical industry reduces the impact on the environment during synthesis 7-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

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