Analyzing the synthesis route of 496-15-1

The chemical industry reduces the impact on the environment during synthesis Indoline. I believe this compound will play a more active role in future production and life.

Reference of 496-15-1, 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. 496-15-1, name is Indoline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of indoline (12) (1.19 g, 10.0 mmol) in sulfuric acid stirred at 0oCwas added KNO3 (1.2 g, 12.0 mmol) in several portions over 15 mins and the reactionmixture was stirred for 1 hr at this temperature and then heated to room temperature foranother 1 hr. After the reaction completed, the mixture was poured into ice-water, andextracted with AcOEt. The organic phase was washed with water and saturatedNaHCO3, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to give the 6-nitroindoline intermediate (13) 0.8 g, yield: 48.8%. 1H NMR (400 MHz, DMSO-d6) delta 7.38 (d, J = 7.9 Hz, 1H), 7.20 (d, J = 7.9 Hz, 1H), 7.15 (s, 1H), 6.15 (s, 1H), 3.53 (t, J = 8.6 Hz, 2H), 3.01 (t, J = 8.6 Hz, 2H). MS (ESI) m/z: 165 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Indoline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem