Indolines-derivatives

Synthetic Route of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Preparation of 8-piperidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and piperazine (0.40 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 431 mg of pure product were obtained. Yield 63percent.

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

Example 37 Preparation of intermediate E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one To the mixture of 6-chlorooxindole (3.3 g, 20 mmol) (Crescent) and 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal (6.5 g, 26.6 mmol) in methanol (150 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (10 g, 46 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (25-33% EtOAc in hexanes) to give E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one as a off white solid (Yield 3.6 g, 46%).

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; Liu, Jin-Jun; Zhang, Jing; Zhang, Zhuming; US2011/201635; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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. Safety of 4,7-Dichloroindoline-2,3-dione

General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18711-13-2, its application will become more common.

Reference:
Article; Naskar, Subhendu; Roy, Suprakash; Sarkar, Swarbhanu; Synthetic Communications; vol. 44; 11; (2014); p. 1629 – 1634;,
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Synthetic Route of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(l,3-dioxoisoindolin-2-yl)acetaldehyde (product of step-3, 4.0 g, 21.15 mmol) in ethanol (40 mL), added hydroxylamine hydrochloride (2.930 g, 42.305 mmol) followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at room temperature for 16 h. The solvent was stripped off, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL) followed by brine, dried over sodium sulphate and concentrated under vacuum to get the title compound (3.2 g, 74percent) as an off white solid. LCMS: m/z 204.1 [M+H] +; NMR (300 MHz, DMSO-d6) delta 11.36 (s, 1H), 7.98 – 7.78 (m, 4H), 6.83 (t, / = 3.8 Hz, 1H), 4.39 (dd, / = 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, Recommanded Product: 129487-92-9

A mixture of 2-chloro-6-methylnicotinic acid (3.43 g), tert-butyl 5-AMINO-1-INDOLINECARBOXYLATE (5.15 g), 1- hydroxybenzotriazole hydrate (3.21 g) and 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE (3.26 g) in N, N- dimethylformamide (30 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate and n-hexane (6: 4 v/v). The eluted fractions containing the desired product were collected and evaporated in vacuo to give tert-butyl 5-{[(2- chloro-6-methyl-3-pyridinyl) carbonyl] AMINO}-1- indolinecarboxylate (6.65 g). 1H-NMR (DMSO-d6) : 8 1.51 (9H, s), 2.51 (3H, s), 3.07 (2H, T, J=8.5 Hz), 3.91 (2H, t, J=8.5 Hz), 7.37-7. 41 (2H, m), 7.52-7. 69 (2H, m), 7.92 (1H, d, J=7.6 Hz), 10.43 (1H, s)

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:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
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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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

Into a 1000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2- yl)propanoic acid (40 g, 182.49 mmol, 1.00 equiv) in water (250 mL). This was followed by the addition of aniline (17 g, 182.55 mmol, 1.00 equiv). To this was added sodium carbonate (9.6 g, 90.57 mmol, 0.50 equiv). The resulting solution was stirred for 3 h at 25 C. The pH value of the solution was adjusted to 5-6 with hydrochloric acid (1 mol/L). The solids were collected by filtration. The filter cake was washed with 1×200 mL of water. This resulted in 40 g (74%) of 3-(l,3-dioxo- 2,3-dihydro-lH-isoindol-2-yl)-N-phenylpropanamide as a white solid. MS (ESI) m/z 295 ([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 3339-73-9.

Reference:
Patent; REXAHN PHARMACEUTICALS, INC.; LEE, Young Bok; KIM, Jae Min; KIM, Deog Joong; AHN, Chang-Ho; WO2014/143960; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 132898-96-5, 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. 132898-96-5 name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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.

Step 1: 5-{[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a stirred cold suspension of 2,3-dioxo-2,3-dihydro-1H-indol-5-sulfonyl chloride (5.00 g, 20.4 mmol) in a 1:1 mixture of THF: CHCl3 (140 mL) was added dropwise, via syringe pump, a solution of N,N-diisopropylethylamine (7.11 mL, 40.8 mmol, 2 eq) and (R)-2-(Methoxymethyl)pyrrolidine (3.27 mL, 26.5 mmol, 1.3 eq) in CHCl3 (60 mL) over a period of 1.5 hours with cooling in an ice bath. After stirring an additional 1 h, the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 95/5 CH2Cl2/CH3OH followed by a second chromatography on silica gel eluding with EtOAc to give 4.21 g (63.8%) of the title compound. NMR (400 MHz, DMSO-d6): consistent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dioxoindoline-5-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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.

To a stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-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 101207-45-8, SDS of cas: 101207-45-8

General procedure: To the mixture of B(C6F5)3 (5.0mol%) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.

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; Ding, Guangni; Wu, Xiaoyu; Lu, Bin; Lu, Wenkui; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 74; 11; (2018); p. 1144 – 1150;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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. Product Details of 5332-26-3

By preheating the internal reactor is sufficiently dried, after substituting dry nitrogen, into the reactor, 4-[ (2-methacryloyloxy) halogenoethoxy]-4-aminobutyric oxopiperidine 11. 51g (0. 05mol), triethylamineborane 6. 07g (0. 06mol), dimethyl formamide (DMF) 150 ml is added. By heating the oil bath 65 C, while stirring, N-(bromomethylbiphenyl) tetrafluorophthalimide 12. 00g (0. 05mol) dissolved in 15 minutes to DMF100mL is added. After the first period, by distilling evaporator DMF, residue extracted with ethyl acetate is obtained. The extract is washed with water to 3 times, then the saturated aqueous solution of sodium bicarbonate, saturated saline successively washed, dried with sodium sulfate (desiccant). Furthermore, after the drying agent is then filtered by a Buchner funnel, distilling organic solvent. In this way, the eq. (M-20) shown (1, 3-dioxo isoindolin-2-yl) methyl 2-(methacryloyloxy) ethyl succinate (13. 95g (yield 72%))is obtained.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JSR CORPORATION; ASANO, YUSUKE; SATO, MITSUO; (60 pag.)JP2015/38072; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem