Indolines-derivatives

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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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;,
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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;,
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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;,
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Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-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 99365-40-9, Product Details of 99365-40-9

Reaction condition three: Under the protection of nitrogen,6-bromopyridin-2-one (212.0 mg, 1.0 mmol),Potassium carbonate (276 mg, 2 mmol),Tetrabutylammonium bromide (33 mg, 0.1 mmol) was placed in a two-neck reaction flask.Sealing the reaction unit,The nitrogen gas was exchanged three times and a nitrogen balloon was inserted.Inject 22 mL of tetrahydrofuran,Stir at 85 C for 30 min,Then slowly inject 3 mL of bromohexane,Stir at 85 C for 8 h.After the reaction was slowly cooled to room temperature, it was poured into ice water and quenched. The organic phase was extracted with dichloromethane and washed three times with water.After suction filtration, the organic phase was concentrated under reduced pressure in vacuo to give a crude material, which was purified by column chromatography chromatography (DCM/PE = 1:1).To give a white waxy solid compound 1-hexyl-6-bromo – indol-one (172mg),The yield was 58.1%.

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

Reference:
Patent; Nanjing University of Posts and Telecommunications; Lai Wenyong; Meng Cheng; Li Xiangchun; Huang Wei; (15 pag.)CN108948026; (2018); A;,
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Reference of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

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 chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

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;,
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Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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. Product Details of 3676-85-5

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 benzoylchloride and 1.20 mmol of triethylamine, then heated under reflux for 6 hours. After cooling, the solid that separates was collected by filtration, then dried under vacuum and purified by crystallization in ethanol. 250.3 mg of the desired product of the title were so obtained (yield 94%). It was characterized by chemical-physical and spectroscopical data. (0165) M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 7.649 (t, 1 H, Ar, J=7.25), 7.825 (t, 2H, Ar, J=7.69), 7.825 (d, 2H, Ar, J=8.32), 7.993 (d, 1 H, Ar, J=7.04), 8.145 (dd, 1 H, Ar, J=7.76, J=1.722), 8.331 (s, 1 H, Ar), 10.792 (s, 1 H, NH, exc), 11.269 (s, 1 H, NH, exc).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3676-85-5, its application will become more common.

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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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. 153171-22-3, name is 2-(4-Bromobenzyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 153171-22-3

N-(4-Phthalimidomethyl)phenyl isatin A solution of 1.863 g (12.66 mmol) of isatin in 80 ml of anhydrous N,N-dimethylformamide (DMF) was treated at room temperature with 0.608 g (15.19 mmol) of sodium hydride (60% dispersion) for about 40 minutes until the formation of the hydrogen bubble ceased. Then, cuprous iodide (CuI, 5.303 g, 27.85 mmol) and 4-phthalimidomethyl bromobenzene (6 g, 18.99 mmol) were added; the reaction was allowed to stir under nitrogen at 160 C. for 16 hours. The reaction was cooled down to room temperature and mixed with 400 ml of chloroform. The resulting mixture was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was separated on a silica flash column (5 to 20% ether/toluene) to give the desired product in 1.76 g (36.4% yield). Rf: 0.2 (silica gel, 10% ether/toluene). MS (MALDI-TOF): m/z 384.437 (observed).

The synthetic route of 153171-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Corporation; US6165800; (2000); A;,
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Electric Literature of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified silica chromatography, eluting with 0-20% EtOAc in hexanes. Desired fractions were concentrated in vacuo to afford the title compound, 1-23. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

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; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
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