Indolines-derivatives

Reference of 423116-18-1, 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. 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Sodium cyanoborohydride (48.5 g, 772 mmol) was added portionwise to a solution of 2-((4-oxocyclohexyl)methyl)isoindoline-1,3-dione (100 g, 389 mmol, Intermediate 28) in AcOH (1.0 L), and the resulting mixture was stirred at rt for 16 h. After this time, the mixture was concentrated, and the concentrate was dissolved in EtOAc. The resulting solution washed twice with a saturated aqueous NaHCO3 solution, dried with anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a colorless solid, which was used in the next step without further purification.

The synthetic route of 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Tanis, Virginia M.; Woods, Craig R.; Fourie, Anne M.; Xue, Xiaohua; (120 pag.)US2019/382354; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, 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 7147-90-2 as follows.

The intermediate compound 4 (0.0165 mol) was dissolved in 40 ml of methylene chloride, cooled to 0 C in an ice bath and triisopropylchlorosilane (0.1818 mol) was added under nitrogen, triethylamine (0.0182 mol) Heated at 40 C for 6 hours and cooled to room temperature. The filter cake was washed with dichloromethane. The filtrate was washed three times with 10% hydrochloric acid solution in 20 ml, and the mixture was washed three times with 20 ml of water. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was steamed to remove the solvent. The residue was washed with a small amount of methanol,Filtered to a yellow solid which was used directly in the next step without purification.

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromoisatin

Take 4-bromoindole dione 2.0g (8.85mmol) into a 25mL round bottom flask, add 5mL N, N-dimethylformamide, was added with stirringK2CO3 3.66g (26.5mmol), and finally added methyl iodide (10.6mmol) at room temperature for 4h.After completion of the TLC detection reaction, 15 mL of water was added to the reaction solution, which was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate,Using developing solvent petroleum ether: ethyl acetate = 5: 1,200-300 mesh silica gel column chromatography to give 2.8 g of 1-methyl-4-bromoindodione, yield 67percent.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tianjin University of Science and Technology; Yu Peng; Sun Hua; Han Kailin; Li Yashan; Peng Xiaolin; Teng Yuou; Zhang Yazhou; (26 pag.)CN104725372; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, 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 1074-82-4 as follows.

Synthesis of Compound 32.1 [0281] To a solution of potassium l,3-dioxoisoindolin-2-ide (18.5 g, 0.1 mol, 1.0 eq) in acetone (200 mL) was added 1,6-dibromohexane (43.5 g, 0.18 mol, 1.8 eq). The mixture was stirred at 65 C for 12 h. After cooling down, the mixture was filtered to remove the precipitated salt. The filtrate was concentrated and the residue purified by a short silica gel column (PE : EA = 10 : 1) to remove the excess 1,6-dibromohexane. 16.1 g of 32.1was obtained as a yellow oil (yield: 52%). 1H NMR (400MHz, DMSO- 6)D delta: 7.88-7.82 (m, 4H), 3.58-3.49 (m, 4H), 1.81-1.74 (m, 2H), 1.63-1.55 (m, 2H), 1.44-1.27 (m, 4H); ESI-MS (M+H) +: 312.1.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
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. 1914-02-9, name is 3,3-Dimethylindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H13N

Example 1 N-(3,3-Dimethylindolin-1-yl)-3-(4-imidazolyl)propionamide monohydrochloride (E1) A suspension of 3-(4-imidazolyl)propionic acid monohydrochloride (2.0g) (Chem. Ber. 66 , 156 [1933]) in thionyl chloride (10ml) and DMF (3 drops) was stirred at room temperature for 3h. The excess thionyl chloride was removed by rotary evaporation and the residue re-evaporated with 2 x 50ml of dry toluene. The residue was suspended in CH2Cl2 (100ml) and a solution of 3,3-dimethyl indoline (1.7g) and triethylamine (4ml) in CH2Cl2 (50ml) was added with stirring and cooling. The reaction mixture was stirred overnight, washed with saturated NaHCO3 and the lower organic layer dried (Na2SO4). Concentration of the organic extracts afforded the crude product which was purified by column chromatography on silica, eluding with CHCl3 containing increasing quantities of methanol.

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 1914-02-9.

Reference:
Patent; BEECHAM GROUP PLC; EP387431; (1990); 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 2-(8-Bromooctyl)isoindoline-1,3-dione

General procedure: To asolution of intermediate 12 (2.0 mmol) andanhydrous K2CO3 (0.69 g, 5.0 mmol) in acetone (10 mL), pyrrolidine(2.5 mmol) was added. After reflux for 6 h until thestarting material 12 disappeared,the solvent was removed under vacuum, the residue was poured into water andextracted with EtOAc, the solution was dried over Na2SO4and then concentrated, the compounds 13 wereused without further purification.

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; Luo, Wen; Wang, Ting; Hong, Chen; Yang, Ya-Chen; Chen, Ying; Cen, Juan; Xie, Song-Qiang; Wang, Chao-Jie; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 17 – 26;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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.

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, m.p. 196-198 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloroisatin, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4730004; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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 24566-79-8, Product Details of 24566-79-8

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained.

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, N-(6-Bromohexyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methoxyindoline (202 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.34 mL, 2.0 mmol) in 4.0 mL of dry dichloromethane was added benzoyl chloride (0.23 mL, 2.0 mmol) at 0 C. After the reaction mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30) to obtain 5-methoxy-1-benzoylindoline (224 mg, 65%).

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, 5-Methoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5,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.

Example 87 N’-(2-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Palladium hydroxide (one small spatula) was added to a solution of the crystal (100 mg, 0.29 mmol) of the compound prepared in Example 86 (mixed with 4-aminophthalimide) in DMF, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. Methanol was added to the residue, followed by filtration to give the title compound as a crystal (27 mg, 29.7%). MS m/z: 310 1H-NMR delta: 4.19 (2H, d, J = 5.37 Hz), 5.09 (2H, s), 6.52 (1H, t, J = 7.32 Hz), 6.63 (1H, d, J = 7.32 Hz), 6.72 (1H, t, J = 5.73 Hz), 6.97 (1H, dt, J = 1.46, 7.56 Hz), 7.04 (1H, d, J = 7.56 Hz), 7.59 (1H, dd, J = 1.95, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 8.01 (1H, d, J = 1.95 Hz), 9.28 (1H, s), 11.08 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem