Category: indolines-derivatives

Application of 3335-98-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3335-98-6 name is 1-Phenyloxindole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyloxindole, and friends who are interested can also refer to it.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20870-79-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20870-79-5 name is 5-Nitroindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

5-Nitro-1,3-dihydro-indol-2-one (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of 5-amino-1,3-dihydro-indol-2-one as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US6846839; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Acetylindolin-3-one

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of Isatin 1a (1 mmol) in water (20 ml)at 60 °C was added o-phenylenediamine 2 (1 mmol). The resulting mixture was stirred and beta-cyclodextrin(15 molpercent) was added to the solution. The reaction progress was monitored using TLC by mixture of Hexane ? EtOAc (6/4). The completion of the reactionas indicated by TLC in UV-chamber and vapour iodine chamber. The reaction mixture was cooled to room temperature and mixture was extracted by ethyl acetate(2 30mL) and dried over anhydrous sodium sulfate.Ethyl acetate removed in vacuum and crude product obtained. To recycle beta-cyclodextrin, acetone was added in the aqueous media, beta-cyclodextrin recovered. Pure product (6H-Indolo[2,3-b]quinoxaline3a) was obtained by silica gel column chromatography(Hexane/EtOAc) = (7/3 ? 6/4) as solid.

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

Reference:
Article; Shivhare, Km Neha; Siddiqui; Supramolecular Chemistry; vol. 31; 1; (2019); p. 52 – 61;,
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Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-(Trifluoromethoxy)indoline-2,3-dione

0.4 mmol of 5-trifluoromethoxyisatin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under an oil bath of 80 C for 29 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-7 (yellow solid, yield 65%, purity 99.8%) was obtained.

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 169037-23-4.

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-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 17702-83-9, Recommanded Product: 2-(8-Bromooctyl)isoindoline-1,3-dione

a) Preparation of 8-(cis/trans-2,6-dimethyl)morpholinyloctyl phthalimide 8-Bromooctylphthalimide (9 g; 26.60 mmoles) and 2,6-dimethyl morpholine (cis-trans isomers mix) (9.8 ml; 79.5 mmoles) were dissolved in anhydrous acetonitrile (50 ml). The mixture was allowed to stir at room temperature for 18 hours approx. The reaction was discontinued by solvent evaporation under reduced pressure. The collected residue was purified by chromatography on silica gel (CH2Cl2/MeOH 95:5). The first product isolated (Rf = 0.7) is a light yellow oil (A trans) (2.04 g), the second (Rf = 0.4) is a yellow oil (B cis) (3.4 g). Total yield 54.8percent.

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, 2-(8-Bromooctyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6ClNO2

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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.

9.30 g (213 mmol) of sodium hydride (purity 55%) and 100 mL of dehydrated DMF were added to a 500 mL two-necked flask, and a solution of 5-nitroindoline in DMF (5-nitroindoline: 35.0 g 213 mmol), DMF: 100 mL) was added dropwise so as not to exceed 30 C. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. To this reaction solution, a DMF solution of 4-fluoronitrobenzene (4-fluoronitrobenzene: 33.0 g (234.5 mmol), DMF: 100 mL) was added dropwise, and the mixture was stirred at room temperature for 6 hours under a nitrogen atmosphere.After completion of the reaction, 100 mL of pure water was slowly poured while stirring the reaction solution, and a solid was precipitated. The precipitated solid was filtered, dissolved again in DMF, poured into 500 mL of pure water, reprecipitated, and the solid was again collected by filtration and recovered . The obtained solid was dispersed and washed with methanol and n-hexane, and vacuum dried to obtain 54.7 g (yield: 90%) of an orange solid.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; NODA, TAKAHIRO; TETSUTANI, HISASHI; (51 pag.)JP5839200; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is Indolin-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 59-48-3, Computed Properties of C8H7NO

Synthesis of 5-acetyl-1,3-dihydro-indol-2-one is described by Peng Cho Tang (US2003/0069421 A1). This compound was prepared according to this procedure from 6.65 g (50 mmol) of 1,3-dihydro-indol-2-one, aluminium trichloride (150 mmol) and acetyl chloride (100 mmol) to give, after trituration in water and drying, 7.32 g (83%) of 5-acetyl-1,3-dihydro-indol-2-one in the form of a beige solid.

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

Reference:
Patent; Pierre Fabre Medicament; US2009/42876; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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.

[0214] In order to preparation the phthalimidomethyl quarternary salt of Compound 1101, a mixture of 100 mg Compound 1101 and 100 mg sodium iodide (2.0 equivalents) were dissolved in 3.0 ml dry acetonitrile. To the mixture was added 128 mg of chloromethylphthalimide and the vial was heated in an oil bath at 55 C for four days. The product was identified by LCMS as a new peak with RF= 3.984, M+ = 467

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; SEMAFORE PHARMACEUTICALS, INC.; GARLICH, Joseph, R.; DURDEN, Donald, L.; WO2004/89925; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem