Category: indolines-derivatives

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;,
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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. 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;,
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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;,
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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;,
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Application of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Di-tert-butyl dicarbonate (54.6 g, 0.25 mol) and sodium hydrogen carbonate (75.6 g, 0.90 mol) were added to a solution of 5-nitroindolin-2-one (17.8 g, 0.10 mol) in 1500 mE THF at room temperature in a nitrogen atmosphere and were stirred for 67 h. The mixture was then stirred for a further 50 h at 50 C., and the reaction solution was then filtered. The filtrate was evaporated until dry, and water was rubbed into the residue, which was then sucked away again and rinsed again with watet Afier the drying in a vacuum, tert-butyl 5-nitro-2-oxo-indolin-1 -carboxylate in the form of a light-brown powder was obtained (20.8 g, 75%). ?RNMR (300 MHz, d6-DMSO): oe=1.61 (s, 9R,tHu), 3.87 (s, 2R, H2), 7.89 (d, 1R, H7), 8.20 (s, 1R, H4),8.25 (d, 1R, H6). ?3C NMR (100 MHz, DMSO): 28.0 (CR3), 36.3(C2), 84.8 (C(CH3)), 114.9 (C7), 120.1 (C4), 124.4 (C6),126.5 (C9), 143.8 (C5), 146.6 (C8), 148.8 (C=O), 177.0(C2).

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); A1;,
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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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 24566-79-8

[0691] Step 2: Synthesis of S-(6-(1,3-dioxoisoindolin-2-yl)hexyl) ethanethioate (4-i) To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassium thioacetate (2.78 g, 34.3 mmol) portion wise and stirred for 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 mL) and stirred for 1 h. The resultant precipitated was filtered, washed with water (100 mL) and dried in vacuo to afford 4-i as an off-white solid (5.8 g, 93.5%). LCMS: 306.20 (M+1).

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); A1;,
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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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 7-Chloroisatin

General procedure: A mixture of 5-chloroisatin (1.81 mg,10 mmol), 1-bromobutane (2 mL, 18 mmol) and cesium carbonate (13.03 g, 40 mmol) in dimethylformamide (100 mL) was stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with hydrochloric acid (0.4 N) and water, dried over MgSO4 and concentrated under vacuum, giving a residue that was washed with a mixture of heptane?ethyl acetate to afford 1-butyl-5-chloroindoline-2,3-dione (2a, 2.13 g, 90percent) as a red solid. The same procedure was used to prepare 2b?d.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, Sanapalli Subba; Pallela, Ramjee; Kim, Dong-Min; Won, Mi-Sook; Shim, Yoon-Bo; Chemical and Pharmaceutical Bulletin; vol. 61; 11; (2013); p. 1105 – 1113;,
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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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C9H6BrNO2

General procedure: S-alkylation of the products was achieved by following a modified method [38]. The oxadiazoles (6a, 6b, 13) (0.02, mol) and K2CO3 (0.022, mol) were stirred in 10mL of acetone for 20 mints followed by the addition of alkyl bromides 7a-c and 7d-m (0.022, mol). The reaction mixture was stirred for 4-6h at room temperature. The reaction mixture was concentrated under vacuum and crude solid gained was recrystallized from methanol to get pure products.

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; Batool, Farwa; Hamdani, Syeda Shamila; Hameed, Shahid; Khan, Bilal Ahmad; Mughal, Ehsan Ullah; Saeed, Muhammad; Saleem, Hafiza Nosheen; Bioorganic Chemistry; vol. 96; (2020);,
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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. 153171-22-3, name is 2-(4-Bromobenzyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(4-Bromobenzyl)isoindoline-1,3-dione

(b) The reaction mixture of 2-(4-bromobenzyl)isoindole-1,3-dione (5.01g, 15.83mmol) and H2NNH2·H2O (100%) (1.59g, 31.67mmol) in MeOH (50ml) was stirred for 1h at reflux. After cooling, MeOH was removed under reduced pressure. Concentrated HCl (20ml) was then added and the resulting mixture was stirred for 1.5h at reflux. After cooling, 2N NaOH (200ml) was added to the mixture, and the insoluble matters were removed by filtration. The filtrate was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and then brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford 4-bromobenzylamine (2.73g, 14.65mmol, y. 93%) as a yellow oil. 1H NMR (300MHz/CDCl3) delta 3.83 (2H, s, CH2), 7.20 (2H, d, J=8.4Hz, ArH), 7.45 (2H, d, J=8.4Hz, ArH).

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

Reference:
Article; Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3720 – 3731;,
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Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

PREPARATION 10; 6-Chloro-5- (3-chloro-propionyl)-1, 3-dihvdro-indol-2-one; A 500mL RB flask equipped with a stirrer, reflux condenser and heating mantle, was charged with aluminum chloride (AICI3) (14.76 g, 0.11 mol), 75 mL of carbon disulfide and 3-chloropropionyl chloride (2.21 mL, 0.023 mol) and this was stirred at rt during the portionwise addition of 6-chloro oxindol (3.0 g, 0.0179 mol). This mixture was then heated to reflux for 3 hours, then cooled. The solvent was decanted and the reaction was quenched with addition of ice and water. The suspension was stirred vigorously for 0.5 hours, followed by filtration. The solids were washed with water and then dried overnight in a vacuum oven. Yield = 4.23 g (92%); MS (APCI), (M + 1) + = 259. 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-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/66165; (2005); A1;,
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