Category: indolines-derivatives

Reference of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

1.00 mmol of 5-aminoisoindoline-1 ,3-dione, commercial product, was solubilized in 1.0 ml_ of toluene and added with 1.20 mmol of commercial 4- chlorobenzoylchloride and 1.20 mmol of triethylamine, then heated at reflux for 10 hours. After cooling, the solid that separates was collected by filtration, dried under vacuum and purified by crystallization in methanol. 285.5 mg of the desired product of the title were so obtained (yield 95%). It was characterized by chemical-physical and spectroscopical data. M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 8.318 (d, 1 H, Ar, J=1.64), 8.131 (dd, 1 H, Ar, J=8.24, J=1.84), 8.024 (d, 2H, Ar, J=8.60), 7.838 (d, 1 H, Ar, J=8.16), 7.659 (d, 2H, Ar, J=8.61), 10.844 (s, 1 H, NH, exc), 1 1.272 (s, 1 H, NH, exc).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; UNIVERSITA’ DI PISA; PAOLINI, Edoardo; QUATTRINI, Luca; COVIELLO, Vito; ANTONIOLI, Luca; FORNAI, Matteo; BLANDIZZI, Corrado; OH, Won Keun; LA MOTTA, Concettina; (30 pag.)WO2018/189679; (2018); A1;,
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Reference of 56341-37-8, The chemical industry reduces the impact on the environment during synthesis 56341-37-8, name is 6-Chlorooxindole, I believe this compound will play a more active role in future production and life.

A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added to a solution of 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) in tetrahydrofuran(5mL) under argon atmosphere, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6):delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1555018; (2005); A1;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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. COA of Formula: C14H16BrNO2

General procedure: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
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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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 317-20-4

7-Fluoro-N-methylisatin (IVa). To a solution of IIIa (380 mg, 2.30 mmol) in dry acetone (60 mL) was added Na2CO3 (anh.) (3.5 g) and dimethylsulfate (0.4 mL) under Ar and the reaction mixture was heated at 60 C. for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C.). The solid residue was submitted to flash chromatography with CH2Cl2 to afford IVa (288 mg, 1.61 mmol, 70%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE PIERRE ET MARIE CURIE; UNIVERSITE DE RENNES I; UNIVERSITY OF LLEIDA; UNIVERSITE D’ATHENES; US2010/331327; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-2-one, 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 7699-18-5, name: 5-Methoxyindolin-2-one

General procedure: The appropriate indolin-2-one (10 mmol) was dissolved in methanol (100 mL) and treated with the equivalent of the appropriate imidazo[2,1-b]thiazole-5-carbaldehyde 2 and piperidine (1 mL toobtain compounds 6, 8, 10) or 37% hydrochloric acid (1 mL to obtain compounds 7, 9). The reaction mixture was refluxed for 8-13 h (according to a TLC test), and the precipitate formed on cooling was collected by filtration.

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, 5-Methoxyindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Conti, Ilaria; Morigi, Rita; Locatelli, Alessandra; Rambaldi, Mirella; Bua, Gloria; Gallinella, Giorgio; Leoni, Alberto; Molecules; vol. 24; 6; (2019);,
Indoline – Wikipedia,
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Electric Literature of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Equimolar quantity of 5-substituted-1H-indolin-2-ones and 2-(4-formylphenoxy)-N-substituted-phenyl-acetamide was taken into round bottom flask containing 50 mL of methanol, followed by 2-3 drops of piperidine. The reaction mixture was refluxed for 1-4 h or till the end of reaction as confirmed by TLC. Then, it was cooled to room temperature and, the solution was filtered. The obtained residue was recrystallized by using dimethylformamide and ethanol.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bhadauria, Vivek Singh; Sravanthi, Vishnu; Kumar, Sujeet; Das, Debajyoti; De Clercq, Erik; Schols, Dominique; Tokuda, Harukuni; Karki, Subhas S.; Acta poloniae pharmaceutica; vol. 74; 1; (2017); p. 137 – 145;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

52351-75-4, name is 6-Methoxyindoline-2,3-dione, 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. SDS of cas: 52351-75-4

General procedure: Suitable indoline-2,3-dione 1a-c (1.0 mmol) was dissolved in methanol (5 mL) with gentle heating, then arylhydrazine (2.4 mmol) was slowly added with stirring at room temperature. After stirring overnight, the resulting precipitate was filtered and crystallized or the reaction mixture was evaporated to dryness and the residue suitably purified.

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Campagna, Francesco; Catto, Marco; Purgatorio, Rosa; Altomare, Cosimo D.; Carotti, Angelo; De Stradis, Angelo; Palazzo, Gerardo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 275 – 284;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-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 611-09-6, Application In Synthesis of 5-Nitroindoline-2,3-dione

General procedure: Dimedone (0.280 g, 2 mmol) and isatin (0.147 g, 1 mmol) weremixed in oxalic acid: proline LTTM (5 mL) as solvent and the resultantmixture was heated at 90 C for appropriate time. After the completionof the reaction indicated by TLC, mixture was stirred at room temperatureand 5 mL distilled water was added. The insoluble crude productwas filtered, washed with distilled water and recrystallized from ethanolto obtain pure product.

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:
Article; Chandam; Patravale; Jadhav; Deshmukh; Journal of Molecular Liquids; vol. 240; (2017); p. 98 – 105;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H9Cl2NO

5. Preparation of ZPR in the melt of Na C03 decahydrate. To the melt of Na2C03 decahydrate (40g) was added BITP HCl (lOg) and CEI (10.35g) and the mixture was heated at 95 C for 10 hours. After 10 h the conversion to ZRP was 88. 2% (% area by HPLC). To the reaction mixture water was added and the solid was filtrated and washed with water. After drying the solid weighs 17.14g (purity by HPLC 88%).; 7. Preparation of ZPR in the presence of NaCl. In a three necked flask was charged 40 ml brine, BITP HC1 (14. 1g), CEI (10.35g) and Na2C03 (14. 1g) ; the mixture was than heated at 90C for 16hours. After this the mixture was cooled, water was added and the solid was filtrated, washed with water and dried. The product weights after drying 16.9g (purity by HPLC 87.5%).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 99365-40-9, A common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

Commercially available 6-bromoxindole (656 mg), zinc cyanide (288 mg) and tetrakis triphenylphosphine palladium(0) (175 mg) were suspended in dry N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three pump/vent cycles with argon and then placed in a preheated oil bath (80 C.). After stirring at this temperature for 15 h the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with water (2×60 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (385 mg; 81%). [MH]+=159.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem