Tag: M.W=100-200

A common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, its 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. 603-62-3.

Compound 25-2: A mixture of 4-nitroisoindoline-1,3-dione (25 g, 130.1 mmol), NaBH4 (11.13 g, 294.0 mmol) in MeOH (250 mL) was degassed and purged with N2 3 times. The mixture was stirred at 25 C. for 2 h under an N2 atmosphere. The solution was acidified with 20% HCl (100 mL) and the reaction mixture was concentrated under reduced pressure to give a residue. The dried residue was treated with acetone. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 0:1). Compound 25-2, 3-hydroxy-4-nitroisoindolin-1-one (15 g, 59% yield) was obtained as a yellow solid.

The synthetic route of 3-Nitrophthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cervello Therapeutics LLC; Lee, Matthew Randolph; Varano, JR., Anthony Joseph; (53 pag.)US2020/140412; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1914-02-9 as follows. 1914-02-9

Intermediate 66 (300mg, 1.2mmol), 3,3-dimethylindoline (182mg, 1.2mmol) and propan-2-ol (3m1) were sealed in a vial and heated at 70C for 4 hours. The mixture was cooled, at which point a precipitate formed. This was collected and dried via vacuum filtration to afford ethyl 7-(3,3-dimethylindolin-1 -yl)thiazolo[5,4-d]pyrimidine-2- carboxylate, as a yellow solid (322mg, 74%); 1H NMR (400 MHz, CHLOROFORM-d) 5ppm 1.48 (m, 9 H), 4.56 (q, .1=7.33 Hz, 2 H), 4.80 (s, 2 H), 7.31 -7.41 (m, 3 H), 8.65 (d, J-7.78 Hz, I H), 8.75 (s, I H); LC-MS (ESI): (MW)355.0

According to the analysis of related databases, 1914-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; WINTER-HOLT, Jon James; MCIVER, Edward Giles; AMBLER, Martin; LEWIS, Stephen; OSBORNE, Joanne; WEBB-SMITH, Kayleigh; (257 pag.)WO2017/85484; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 496-12-8. 496-12-8

Commercially available benzenesulfonylchloride 6 (500 mg, 2.12 mmol) was dissolved in CH2Cl2 (29 mL), treated with Et3N (0.89 mL, 6.4 mmol) and isoindoline (0.48 mL, 0.51 g, 4.2 mmol) and stirred at room temperature for 3 h. The organic layer was diluted with CH2Cl2, washed successively with 1N aqueous HCl and then dried over anhydrous sodium sulphate. Evaporation under vacuum of the organic solvent afforded a crude product which was purified by column chromatography over silica gel, to yield the sulfonamidic derivative.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Isoindoline.

Reference:
Article; Granchi, Carlotta; Roy, Sarabindu; Mottinelli, Marco; Nardini, Elisa; Campinoti, Fabio; Tuccinardi, Tiziano; Lanza, Mario; Betti, Laura; Giannaccini, Gino; Lucacchini, Antonio; Martinelli, Adriano; MacChia, Marco; Minutolo, Filippo; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7331 – 7336;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 774-47-0

6-Ethylthio-5-fluoroindole-2,3-dione 6-Ethylthio-5-fluoroindole-2,3-dione was prepared from 5,6-difluoroindole-2,3-dione using sodium thioethoxide according to the method described in the synthesis of 5-fluoro-6-methylthioindole as a brown solid (2.53 g, 19%): mp 215 C.; IR numax (Nujol)/cm-1 3286, 2926, 2855, 1766, 1712, 1619, 1467 and 1038; NMR deltaH (400 MHz, DMSO-d6) 1.32 (3H, t, J 7.5 Hz), 3.13 (2H, q, J 7.5 Hz), 6.77 (1H, d, J 6.0 Hz), 7.39 (1H, d, J 8.5 Hz), 10.97 (1H, brs).

The chemical industry reduces the impact on the environment during synthesis 774-47-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Vernalis Research Limited; US6380238; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, its 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. 480-91-1

To a solution of 2,3-dihydroisoindole-1-one (5 g, 38 mmol) in concentrated sulfuric acid (100 ml) at 0 C., KNO3 was added portionwise whilst maintaining the temperature at 0 C. The reaction was gradually allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured into ice and the resulting precipitate was filtered off and dried to give title compound as a yellow solid (4.7 g, 70%). 1H NMR (360 MHz, d6 DMSO) ? 8.96 (1H, s), 8.45 (1H, dd, J=8.3 Hz, 2.2 Hz), 8.34 (1H, d, J=2 Hz), 7.87 (1H, d, J=8.3 Hz), 4.54 (2H, s). m/z (ES+) 179 (M+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 480-91-1.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

52351-75-4, Adding a certain compound to certain chemical reactions, such as: 52351-75-4, name is 6-Methoxyindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 52351-75-4.

6-Methoxylisatin (6 g, 33.87 mmol), 1 -indan-ethanone (40.64 mmol), and o 85% KOH pellets (120 mmol) were dissolved in EtOH (40 mL). The reaction mixture was stirred at 800C for 24 hours. After the solvent was removed by evaporation, the residue thus obtained was dissolved in H2O (50 mL). The solution was then washed twice with Et2O (30 mL). The aqueous phase was cooled by an ice- water bath and acidified with a 37% HCl aqueous solution to pH 1. The precipitate was collected by suction filtration, washed with H2O, and dried to give compound I- 20, 2-indan-5-yl-7-methoxy-quinoline-4-carboxylic acid (9.5 g, 88%) as a solid. ESI- MS (M+H+) = 320.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Methoxyindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAIGEN BIOTECHNOLOGY CO. LTD.; WO2008/95058; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below.

Butyllithium (2.5 M in hexanes, 3.76 mL, 9.39 mmol) was added to a solution of oxindole (500 mg, 3.76 mmol) at -78 0C in TEtaF (40 mL). After complete addition, NJSfJSf1N- tetramethylethane-l,2-diamine (1.48 mL, 9.76 mmol) was added, maintaining the internal temperature < 70 0C. After 1 h at -78 0C, 2-iodoethyl ether (4.90 g, 15.0 mmol) was added and the reaction warmed to ambient temperature. After 48 h the reaction was quenched with H2O (5 mL) and the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous solution was extracted with EtOAc (3 x 50 mL) and the combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of CH2Cl2MeOH- 100:0 to 97:3, gave the title compound. MS: m/z = 204 (M + 1). If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it. Reference:
Patent; MERCK & CO., INC.; WO2006/31610; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3484-35-3, Name is 5-Methylindolin-2-one, 3484-35-3, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: To a solution of s7 (398 mg, 1.18 mmol) in EtOH (2.30 mL) were successively added addedoxindole (105 mg, 1.13 mmol) and piperidine (12 muL, 0.12 mmol) at room temperature. After 20 h,the reaction mixture was concentrated in vacuo. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 4/1) to afford aldehyde 1a (422 mg, 84%) as yellowsolid, whose geometry was determined by X-ray crystal analysis.

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3484-35-3, name is 5-Methylindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 3484-35-3

General procedure: A mixture of compound 4 (10 mmol), benzaldehyde (12 mmol) and afew drops of piperidine in ethanol (100 mL) was refluxed for 2 h. Partof the solvent was evaporated under reduced pressure and the residue was cooled to room temperature to crystallise the solid product,which was filtered off, washed twice with ethanol, and dried to yield compound 5.

Statistics shows that 3484-35-3 is playing an increasingly important role. we look forward to future research findings about 5-Methylindolin-2-one.

Reference:
Article; Jiang, Hongwu; Feng, Zhiyuan; Chen, Taiping; Li, Zicheng; Huang, Wencai; Luo, Youfu; Zhao, Yinglan; Journal of Chemical Research; vol. 42; 1; (2018); p. 44 – 49;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 39755-95-8, name is 5-Methoxyisatin, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 39755-95-8. 39755-95-8

Synthesis of l -Benzyl-5-methoxyindolin-2-one[00143] A stirred solution of 5-methoxyisatin (5.0 g, 28 mmol) in dry DMF (40 mL) was cooled in an ice bath before addition of sodium hydride (60 wt% in mineral oil, 1.7 g, 42 mmol) slowly, the dark red solution turning quickly black. After stirring for 20 min, BnBr (3.7 mL, 31 mmol) was added to the reaction mixture by syringe and the resulting mixture was stirred for 1 h. Water (150 mL) was added with stirring, and the resulting dark red precipitate collected by filtration and washed with water to give l-benzyl-5- methoxyindoline-2,3-dione as a dark red solid (6.1 g, 81%). NMR (400 MHz, CDC13) delta 7.39-7.31 (m, 5H), 7.17 (s, 1H), 7.03 (d, J = 8.1 Hz, 1H), 6.68 (d, J = 8.6 Hz, 1H), 4.92 (s, 2H), 3.79 (s, 3H). MS ESI 268.1 [M + H]+, calcd for [C16H13N03+ Hf 268.09.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Methoxyisatin.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem