Author: Jessica.F

Application of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

6-chloroindolin-2-one (8.35 g, 50 mmol) and 3-chloro-2-fluorobenzaldehyde (8.295 g, 52.5 mmol) were stirred at reflux for 6 hours in the presence of piperidine (1 ml). Then filter the reaction suspension, The collected solid was washed with methanol and dried to give (E)-6-chloro-3-(3-chloro-2-fluorobenzylidene)indol-2-one product (14.63 g, 47.5) as a yellow solid. Mmol), yield 95%.

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; Xiao Fei; Ma Jie; Ren Hongjun; Wang Wei; Xu Hongtao; Wang Meng; Zou Lihui; Ding Fei; Su Fei; (37 pag.)CN107698598; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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 169037-23-4, Recommanded Product: 169037-23-4

General procedure: The NiO-SiO2 catalyst (6.5 mol%) was added to a mixture of isatin (1 mmol), malononitrile (1 mmol), and 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol) in EtOH, and the reaction flask was placed in an oil bath and refluxed for the appropriate time. The progress of reaction was monitored by TLC. After the completion of the reaction, the heterogeneous catalyst was recovered from the reaction mixture by filtration. The filtrate was evaporated to afford the crude solid product which was later purified by column chromatography. The solid catalyst was washed with hot EtOH and then dried in oven to reuse.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Yagnam, Swetha; Akondi, Adinarayana Murthy; Trivedi, Rajiv; Rathod, Balaji; Prakasham, Reddy Shetty; Sridhar; Synthetic Communications; vol. 48; 3; (2018); p. 255 – 266;,
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Indoline | C8H9N – PubChem

Related Products of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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.

General procedure: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL¡Á2) to afford the pure products as solid powder in good to excellent yields without further purification.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-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. COA of Formula: C12H12BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

The synthetic route of 5394-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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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. 52537-00-5, name is 6-Chloro-2,3-dihydro-1H-indole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8ClN

General procedure: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3¡Á20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.

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; Wang, Ci-Ping; Jiang, Guo-Fang; Tetrahedron Letters; vol. 58; 18; (2017); p. 1747 – 1750;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of l-[4-(trifluoromethyl)phenyl]methanamine (1.7 g, 9.7 mmol, 1.5 equiv) in trifluoroethanol (10.0 mL) was added 2-(2-oxopropyl)isoindoline-l,3-dione (2.0 g, 9.6 mmol, 1.5 equiv). After stirring at r.t. for 10 min, to the mixture was added 5-chloro-3- fluoro-2-isocyanopyridine (1.0 g, 6.4 mmol, 1.0 equiv) and chloroacetic acid (899.4 mg, 9.5 mmol, 1.5 equiv). The resulting mixture was stirred at 60 C overnight, concentrated under vacuum, and purified by C18 column, eluted with water (0.5%NH4HCO3)/ACN (1/5) to afford 750 mg of /V-(5-chloro-3-fluoropyridin-2-yl)-2-(2-chloro-/V-[[4- (trifluoromethyl)phenyl]methyl]acetamido)-3-(l,3-dioxoisoindol-2-yl)-2-methylpropan amide (Intermediate 64-2) as a yellow oil. LRMS (ES) m/z 611 (M+H).

The synthetic route of 2-(2-Oxopropyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of N-(bromomethyl)phthalimide (3.6g, 15.0mmol) in triethylphosphite (3.00g, 18.0mmol) was heated to 90Cfor 3h. A distillation apparatus was then installed and volatile ethyl bromide was removed by reduced pressure distillation. The crude mixture was cooled to room temperature, and the resulting white solid was used without further purification. 1H NMR (300MHz, CDCl3) delta=1.24 (t, J=7.1Hz, 6H, 2¡ÁCH3), 4.01 (d, 2JH-P=11.4Hz, 2H, 1¡ÁCH2), 4.12 (m, 4H, 2¡ÁCH2), 7.73 (dd, J=5.5, 3.1Hz, 2H, 2¡ÁCH), 7.86 (dd, J=5.3, 3.0Hz, 2H, 2¡ÁCH) ppm. To a solution of this solid (4.5g, 15mmol) in ethanol (20mL) was added hydrazine monohydrate (1.05mL, 21.6mmol) and the resulting mixture was stirred at room temperature overnight, and then refluxed for 3h. The crude mixture was cooled down to 0C, and the white precipitate was removed by filtration and washed with ice-cold ethanol. The solution was concentrated under vacuum, and the resulting oily residue was purified by column chromatography on silica gel eluting with a gradient of Et2O/ MeOH (80:20?70:30) to afford compound 24 as a pale yellow oil (2.43g, 97%). TLC: Rf=0.30 (silica gel, Et2O/MeOH 80:20, stained with ninhydrin). 1H NMR (300MHz, CD3CN) delta=1.31 (t, J=7.1Hz, 6H, 2¡ÁCH3), 1.76 (br, 2H, NH2), 2.94 (d, 2JH-P=10.6Hz, 2H, 1¡ÁCH2), 4.08 (quintet, 3JH-H=3JH-P=7.0Hz, 2H, 1¡ÁCH2), 4.10 (quintet, 3JH-H=3JH-P=7.1Hz, 2H, 1¡ÁCH2) ppm. 31P NMR (121MHz, CDCl3) delta=27.49ppm.

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Leygue, Nadine; Perez e Iniguez De Heredia, Aritz; Galaup, Chantal; Benoist, Eric; Lamarque, Laurent; Picard, Claude; Tetrahedron; vol. 74; 31; (2018); p. 4272 – 4287;,
Indoline – Wikipedia,
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Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

In a dried flask, to a solution of chloroacetone, (10 g, 108 mmol) in DMF (100 mL) was added potassium phthalimide (22 g, 118 mmol) with constant stirring (potassium phthalimide was not completely soluble in DMF). The reaction was stirred at room temperature for 16 h and monitored by TLC. After the reaction was complete, the reaction mixture was poured into water (2500 mL). A white precipitate formed, which was collected by filtration, washed with water until colourless, and dried to afford 21.6 g (99.0% yield) N-acetonyl phthalamide (3). 1H NMR (CDCl3, 600 MHz) delta 7.88-7.87(dd, 2H, J1 = 2.7 Hz, J2 = 5.4 Hz), 7.76-7.75 (dd, 2H, J1 = 2.7 Hz, J2 = 5.4 Hz), 4.51 (s, 2H), 2.27 (s, 3H).

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Ying-Chun; Ren, Zhen-Xing; Zhao, Xue-Feng; Zhang, Yong-Bin; Wang, Jun-Hong; Chao, Jian-Bin; Wang, Meng-Liang; Tetrahedron; vol. 75; 36; (2019);,
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These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. category: indolines-derivatives

The hydrochloride salt of racemic 3-fluoropyrrolidinc (628 mg, 5mmol) was added to a solution of 2,3-oxoindohne-5-sulfonyl chloride (1.2 g, 4.9 mmol) and diisopropylethyl amine (2.6 mL, 15 mmol) in 1 :1 CH2Cl2ZTHF (50 mL) at -50 C. The solution was warmed to room temperature and slirred at that temperature for 12 hours. The reaction mixture was concentrated, dissolved in CII2CI2. and then washed with saturated NaHCO3 and brine. I he organic layer was dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH2Cl2) to provide 1.4 g of the product as an orange solid

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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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 20870-78-4 as follows. Application In Synthesis of 5-Bromoindolin-2-one

A mixture of 28b (513mg, 2.42mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl (l,3,2-dioxaborolan-2-yl))-l ,3,2-dioxaborolane (716mg, 2.82mmol) and KOAc (878mg, 8.95mmol) in dioxane (2OmL) was purged with nitrogen for lOmin, then added Pd(dppf)Cl2. CH2Cl2 (108mg, 0.13mmol). The resulting mixture was stirred at 800C overnight and evaporated. The residue was dissolved in ethyl acetate and filtrated. The filtrate was washed with brine (15mLchi2), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (EA: PE =4:1) to afford 28c (470mg, 75%).

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem