Author: tianli

These common heterocyclic compound, 59-48-3, name is Indolin-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. 59-48-3

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

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 59-48-3.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, Adding some certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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.

Potassium tert-butoxide (6.2 g) was suspended in tetrahydrofuran (55 mL), and a suspension of 6-bromo-1,3-dihydroindole-2-one (2.3 g) in tetrahydrofuran (39 mL) and copper (I) bromide dimethyl sulfide complex (252 mg) were added. To the reaction mixture, methyl iodide (1.9 mL) was added at 0C, and then the reaction mixture was stirred at 0C for 5 minutes, and subsequently stirred at room temperature for 30 minutes. To the reaction mixture, an aqueous solution of ammonium chloride was added, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.4 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.65 (1H, brs), 7.18 (1H, dd, J = 7.8, 2.0 Hz), 7.06 (1H, d, J = 2.0 Hz), 7.05 (1H, d, J = 7.8 Hz), 1.38 (6H, s). ESI-MS found: 240 [M+H]+

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 99365-40-9.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Patent; JEPPESEN, LONE; ANDERSEN, HENRIK SUNE; OLSEN, OLE HVILSTED; JUDGE, LUKE MILBURN; HOLSWORTH, DANIEL DALE; BAKIR, FARID; AXE, FRANK URBAN; GE, YU; US2002/2199; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39755-95-8, 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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of acetophenone or isatin (5 mmol) in THF (10 mL), BF3¡¤OEt2 (7.5 mmol) was added at 0C under the atmosphere of N2 and the mixture was stirred for 10 minutes. To the cooled mixture, anhydrous hydrazine (7.5 mmol) was added in one portion and the reaction mixture was stirred at 0C under the atmosphere of N2 for 30 min. The reaction was quenched by the addition of a saturated solution of NH4Cl (4 mL), extracted by ethyl acetate (3 ¡Á 15 mL) and purified by column chromatography (ethyl acetate-CH2Cl2; 3 : 7) to afford hydrazones 2-22.

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; El-Azab; Ghabbour; El-Husseiny; Maarouf; Mohamed; Abdel-Aziz; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2837 – 2844; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2837 – 2844,8;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

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

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 324-03-8, name is 6-Fluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 324-03-8

General Procedure: To a solution of 4-chloro isatin (500 mg, 2.75 mmol) in acetone (5 mL) was added diethylamine (314 muL, 3.02 mmol) at room temperature. The mixture was heated to 50 oC for 14 hours with magnetic stirring and then concentrated under reduced pressure. The resulting alcohol intermediate was triturated in diethyl ether with sonication, filtered and the resulting white solids were used without further purification. To a solution of the alcohol intermediate dissolved in ethanol (3 mL) was added concentrated hydrochloric acid (1 mL). The mixture was stirred at room temperature for 14 hours and then quenched with a solution of saturated sodium bicarbonate (5 mL). The mixture was extracted with dichloromethane (20 mL), concentrated and purified by silica gel flash chromatography using a gradient of 30 – 80% ethyl acetate in hexanes to afford the target compound 10 as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 324-03-8. I believe this compound will play a more active role in future production and life.

Reference:
Conference Paper; Kloeck, Cornelius; Jin, Xi; Choi, Kihang; Khosla, Chaitan; Madrid, Peter B.; Spencer, Andrew; Raimundo, Brian C.; Boardman, Paul; Lanza, Guido; Griffin, John H.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 9; (2011); p. 2692 – 2696;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

(b) Preparation of 5-Nitro-2-oxindole. The 2-oxindole (6.5 g) was dissolved in 25 mL of concentrated sulfuric acid and the mixture maintained at -10-15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice water. The precipitate was collected by filtration, washed with water and crystallized from 50% of the acetic acid. The final crystal was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

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

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is Indolin-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. 59-48-3

To a solution of indolin-2-one (5 g, 37.55 mmol) and LiCl (5.6 g, 131.4 mmol) in THF (100 mL) was added w-BuLi (2.5 M, 30 mL) at -78 ¡ãC. The mixture was stirred at -78 ¡ãC for 20 min, followed by the addition of Mel (4.8 mL, 75.1 mmol). The reaction was stirred at 25 ¡ãC overnight, then quenched with saturated aqueous NH4C1 (100 mL) and diluted with EtOAc (100 mL x 3). The organic phase was washed with H20 (100 mL) followed by brine (100 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silca gel column chromatography (PE/EtOAc (v/v) = 8/1) to give the title compound as a white solid (2.92 g, 48.3percent). MS (ESI, pos. ion) m/z: 162 [M + H]+; NMR (CDCI3) delta (ppm): 9.23 (s, 1H), 7.21-7.18 (m, 2H), 7.04 (t, 1H), 6.96 (d, 1H), 1.41 (s, 6H).

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 59-48-3.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, 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 118289-55-7 as follows.

Preparation of 5- [2-[4-(1, 2- benzisothiazol-3-yl) -1-piperazipyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one (Ziprasidone base) Example 2 was repeated with the exception that 1-butyl-3-methylimidazolium tetrafluoroborate was used instead of 1-ethyl-3-methylimidazolium methyl sulfate. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC.

According to the analysis of related databases, 6-Chloro-5-(2-chloroethyl)indolin-2-one, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KRKA; EP1889844; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-2-one, 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 20870-78-4. 20870-78-4

Description 3:(Z)-3-{(1H-Pyrrol-2-yl)methylene)-5-bromoindolin-2-oneIn a 35 ml microwave tube were placed 5-bromo-1,3-dihydro-2H-indol-2-one (1 mmol), pyrrole-2-carbaldehyde (1.2 mmol), piperidine (2 drops), ethanol (10 ml) and a magnetic stir bar. The vessel was sealed with a septum and placed in the microwave cavity. Initial microwave irradiation of 200 W was used, the temperature being ramped from RT to 150 C. Once 150 C was reached the reaction vessel was held at this temperature for 30 min by moderation of the initial microwave power. After cooling, solvent was removed in vacuo and ethyl acetate was added to the reaction mixture. The precipitate was collected by filtration and washed with ethyl acetate (2x 10 ml) to afford a yellow-brown solid. The results set out below identify the product as the title compound D3.

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 5-Bromoindolin-2-one.

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem