Category: 496-15-1

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 496-15-1, name is Indoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H9N

PREPARATION 4 6-Nitroindoline 5.96 g (50 mmol) of indoline were dissolved in 25 ml of concentrated sulfuric acid, and a mixture of 3.75 ml of concentrated nitric acid (61%) and 25 ml of concentrated sulfuric acid was added to the solution while ice-cooling so that the internal temperature was maintained at 10 C. or lower. The mixture was then stirred while ice-cooling for 2 hours. At the end of this time, a 75% w/v aqueous solution of sodium hydroxide was added to the reaction mixture while ice-cooling to neutralize the reaction mixture, while maintaining the internal temperature at 60 C. or lower. The mixture was then extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and, after filtration, the solvent was removed from the filtrate by distillation under reduced pressure to obtain 7.8 g (47.5 mmol) of the title compound as crystals, melting at 65-68 C. (yield: 95%). 1 H Nuclear Magnetic Resonance (200 MHz, CDCl3) delta ppm: 3.10 (2H, triplet, J=8.5 Hz); 3.69 (2H, triplet, J=8.5 Hz); 4.04 (1H, broad singlet); 7.15 (1H, doublet, J=8.1 Hz); 7.35 (1H, doublet, J=2.1 Hz); 7.56 (1H, doublet of doublets, J=2.1 & 8.1 Hz).

The synthetic route of 496-15-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5773618; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

Some common heterocyclic compound, 496-15-1, name is Indoline, molecular formula is C8H9N, 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. 496-15-1

COMPARATIVE EXAMPLE 1 1,3-Dihydro-1,3,3-trimethyl-6′-(2,3-dihydroindol-1-yl) spiro[2H-indole-2,3′-3H-naphtho[2,1-b][1,4]oxazine] A mixture of 1-nitroso-2-naphthol (17.3 g; 0.10 mol) and indoline (23.8 g; 0.20 mol) in trichloroethylene (150 ml) was heated under reflux for 10 min. A solution of 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (17.3 g; 0.1 mol) in trichloroethylene (100 ml) was added in one batch and the resulting mixture heated under reflux for 1 h. The solution was evaporatedand the oily residue treated with acetone to yield 1,3-Dihydro-1,3,3-trimethyl-6′-(2,3-dihydroindol-1-yl)spiro [2H-indole-2,3′-3H-naphtho[2,1-b][1,4]oxazine] as a yellow solid (4.44 g; 10%). m.p 255-7 C. STR10

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 496-15-1, its application will become more common.

Reference:
Patent; Pilkington plc; US5446151; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem