Month: June 2021

Application of 20870-79-5, These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-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.

General procedure: To a suspension of 5-nitro-3-substituted-2-oxindole derivatives 8-12 or commercially available 5-nitroindolin-2-one (1 mmol) in amixture of ethanol and water (10 mL, 4:1 v/v) was added iron powder (560 mg.10 mmol,10 equiv.) and NH4Cl (134 mg, 2.5 mmol,2.5 equiv.). The mixture was refluxed for 2 h, cooled and filteredthrough Celite. The filtrate was diluted with water (5 mL) andextracted with dichloromethane (3 x 10 mL). The combinedorganic layers were washed with water (10 mL) and brine (10 mL),dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by crystallization withethyl ether.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romagnoli, Romeo; Baraldi, Pier Giovanni; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Salvador, Maria Kimatrai; Lopez-Cara, Luisa Carlota; Bortolozzi, Roberta; Mattiuzzo, Elena; Basso, Giuseppe; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 258 – 270;,
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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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6-Fluoroindoline-2,3-dione

Add 11.33g NaNO3 and 100mL H2SO4 to a 500mL reaction flask.With stirring, the temperature of the ice bath was lowered to 0 C. Take 20.00g of compound 1-1,Dissolved in 120mL H2SO4,Slowly add the 1-1 H2SO4 solution to the reaction flask,After dripping, the reaction was held at 0 C for 1 hour, and then the reaction solution was poured into 1 L of ice water.After stirring for 0.5 hours, it was filtered and the filter cake was washed with water until neutral.The filter cake was washed with 80 mL of EtOH / H2O (7: 3) for 0.5 hours, filtered,The filter cake was dried to obtain 18.83 g of a crude product of 2-1.Yield: 74%.

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 324-03-8.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Ma Dawei; Wang Kailiang; Xia Shanghua; Li Zheng; Zhao Jinlong; Li Ying; (82 pag.)CN110642874; (2020); A;,
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Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 169037-23-4

Preparation of 3-hydroxy-5-trifluoromethoxy-3-(nitromethyl)indolin-2-one 5-trifluoromethoxy isatin ((0.115 g) and nitromethane (0.1 ml) were added to water and the reaction mixture was vigorously stirred at a temperature of 30 C. for 20 minutes. The obtained product was extracted with ethyl acetate and the solvent was removed to give pure product.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAO, Mandapati Mohan; PRATHIMA, Parvathaneni Sai; US2013/345438; (2013); A1;,
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Indoline | C8H9N – PubChem

Synthetic Route of 1168150-46-6,Some common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, molecular formula is C18H15NO4, 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: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, its application will become more common.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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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

Mg(ClO4)2 (0.1 g) was added to a mixture of isatin (2 mmol), and dimedone (4 mmol) in aqueousethanol solution (50%, v/v, 5 mL), and the resulting mixture was stirred at 80C for 10-12 h. Upon completion of the reaction (TLC, Ethyl acetate/Petroleum ether = 1:4), the mixture was allowedto cool to room temperature. The resulting solid was filtered and washed successively with water(2 30 mL) and cold aqueous ethanol (2 1 mL) to afford a crude product, which was recrystallizedfrom EtOH to afford the pure product 3. Some insolubility could be observed in the refluxing ethanolduring the recrystallization process, which should be filtered when hot.

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; Chen, Chunfeng; Lv, Chunlei; Liang, Jianfeng; Jin, Jianqing; Wang, Lijun; Wu, Chunlei; Shen, Runpu; Molecules; vol. 22; 8; (2017);,
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Related Products of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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.

To a solution OF NAHMDS (1 M THF solution) (800 ml, 0.8 mol), the solution OF 5-METHOXY-1, 3- dihydro-indol-2-one (26.1 g, 0.16 mol) in THF (160 ml) and benzyl-bis- (2-chloro-ethyl)-amine (47.3 g, 0.18 mol) in THF (176 ml) are added AT-78?C. The reaction mixture is stirred for 15 h at room temperature, quenched with saturated ammonium chloride and ice-water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over sodium sulphate and evaporated down. Ethyl ether is added to the residue to give the powder, which is filtrated. Yield: 39 % Rf=0.25 (N-hexane: AcOEt = 1:1). 1H-NMR (400MHz, CDCl3) delta: 1.81-1.99 (m, 2H), 2.00-2.04 (m, 2H), 2.66-2.72 (m, 2H), 2.90-2.96 (m, 2H), 3.67 (s, 2H), 3.77 (s, 3H), 6.71-6.81 (m, 2H), 7.00 (s, 1H), 7.25-7.40 (m, 5H), 8.32 (brs, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxyindolin-2-one, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/76455; (2004); 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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Nitrophthalimide

3-Nitrophthalimide (LOOGR) was taken into a beaker and dissolved using 200ML of dimethylformamide and 300ML of methanol. The solution was transferred into a 1L hydrogenation kettle and 20gr of Raney nickel was charged into the kettle. Hydrogenation was carried out initially at 20-40psi and 25-30C until the exothermic nature was over. Hydrogenation was further continued at 40-60psi pressure and 40-50C. After checking the completion of reaction by TLC catalyst was removed by filtration and the solvents distilled off from the reaction mixture at 50-60C. The residue thus obtained was suspended in water (500ML) and filtered off to get a bright yellow crystalline compound of 3-aminophthalimide (78gr, 92.5%). Melting point: 263-4C

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; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5428-09-1, The chemical industry reduces the impact on the environment during synthesis 5428-09-1, name is 2-Allylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Under argon, a solution of [5-(4-bromo-2,6-dimethyl-phenyl)-[1,2,4]triazin-3-yl]-(5-methoxy-benzothiazol-2-ylmethyl)-amine (46 mg, 0.1 mmol, prepared as in example 79), N-allyl phtalimide (22.5 mg, 0.12 mmol, prepared as in Tetrahedron 2006, 62, 12247), triethylamine (28 muL, 0.2 mmol), tri-o-tolylphosphine (3.6 mg, 0.012 mmol), palladium(II) acetate (1.4 mg, 0.006 mmol) in degassed anhydrous acetonitrile (0.2 mL) was stirred at 100°C overnight. The reaction mixture was filtered over a pad of celite, rinsed with dichloromethane, methanol, ethyl acetate, and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 95/5) to afford 2-[3-(4-{3-[(5-methoxy-benzothiazol-2-ylmethyl)-amino]-[1,2,4]triazin-5-yl}-3,5-dimethyl-phenyl)-allyl]-isoindole-1,3-dione (43 mg, 76percent) as a beige solid. ESI-MS m/z 563 (M+H)+.

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-Allylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mutabilis; EP2141164; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

169037-23-4, name is 5-(Trifluoromethoxy)indoline-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. Computed Properties of C9H4F3NO3

General procedure: The title compound was synthesized in one step from commercially available starting materials according to the following procedure. Into a 20mL microwave reaction vial, containing a magnetic stir bar, were weighed 5-(trifluoromethoxy)isatin (460mg, 2.0mmol), K2CO3 (550mg, 4.0mmol), KI (33mg, 0.20mmol), followed by acetonitrile (20mL, 0.1M) and 2-bromoethyl phenyl ether (480mg, 2.4mmol). After being sealed with a crimp cap, the vessel was placed in a microwave reactor and heated to 160C for 10min, with magnetic stirring. After cooling to ambient temperature, the reaction was diluted with CH2Cl2 (?20mL) and washed with brine. The organic layer was separated and dried over Na2SO4. Solvent was removed under reduced pressure and the crude product was purified via flash column chromatography (silica gel, hexane/ethyl acetate, 0-50% ethyl acetate gradient). Product containing fractions were combined and the solvents removed under reduced pressure to obtain 583mg of ML326 (83% yield) as a red-orange powder. TLC Rf=0.79 (hexane/ethyl acetate 1:1); 1H NMR (400MHz, CDCl3 calibrated to 7.26) delta 7.52-7.46 (m, 2H), 7.31-7.25 (m, 3H), 6.98 (t, J=7.4Hz, 1H), 6.82 (d, 2H), 4.28 (t, J=5.0Hz, 2H), 4.17 (t, J=5.0Hz, 2H); 13C NMR (125MHz, CDCl3 calibrated to 77.16) delta 182.25, 158.27, 157.93, 150.01, 145.44, 131.02, 129.78, 121.75, 118.32, 114.39, 112.89, 65.94, 40.62; HRMS calcd for C17H13NO4F3[M+H+]; 352.0797 found: 352.0795.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gentry, Patrick R.; Bridges, Thomas M.; Lamsal, Atin; Vinson, Paige N.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Engers, Julie L.; Niswender, Colleen M.; Scott Daniels; Jeffrey Conn; Wood, Michael R.; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2996 – 3000;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, Computed Properties of C9H6BrNO2

General procedure: To a stirring mixture of catalyst 1a (0.005 mmol) and cyclohexanone/acetone (5 mmol) in water (500 muL), additive DNP (0.920 mg, 0.005 mmol) was added at 25 C and the mixture was allowed to stir for 5 min followed by addition of isatin derivative (0.5 mmol). The mixture was stirred for 20-96 h and the progress of the reaction was monitored at regular intervals by TLC. On the completion of reaction, saturated solution of NH4Cl (5 mL) was added to it and resulting mixture was extracted with ethyl acetate (3×15 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude aldol product. The column chromatography on silica gel (60-120 mesh) using hexane/ethyl acetate as an eluent gave the corresponding aldol adducts as a syn/anti mixture. The enantiomeric excess of aldol addition products was determined by chiral HPLC. The diastereoselectivity of product was determined by HPLC of crude reaction mixture. Racemic standards were prepared using (±) 3-methyl-1-morpholinobutan-2-amine catalyst synthesized form (±) valine.

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; Kumar, Akshay; Chimni, Swapandeep Singh; Tetrahedron; vol. 69; 25; (2013); p. 5197 – 5204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem