Category: indolines-derivatives

Electric Literature of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Example 7 : 2-({2-[2-(4-{(2S)-2-Hydroxy-3-[(methylethyl)amino]propoxy}phenoxy) acetylamino] ETHOXY} METHYL)-4-(2-CHLOROPHENYL)-5-CYANO-6-METLLYL-1, 4- dihydropyridine-3-carboxylate is synthesized according to Scheme VI. SCHEME VI 0 Ho- p OEt HO out C1 Ni C1 Me NC Me N N CHO CHO ci NC Me H 0 1. acetone, II. — . HO /O 2. II wEthyl 4- [2-FL, 3-DIOXOISOMDOLM-2-YDETHOXY1-3-OXOBUTANOATE. A solution of 2- (2- hydroxyethyl) isoindoline-1, 3-dione (10 g; 52.31 mmol) in DMF (150 ml) is cooled to 0C and treated with 1. 1 equivalents of a 60% dispersion of sodium hydride in mineral oil. After gas evolution has ceased, ethyl 4-chloro-3-oxobutanoate (7.75 g; 47.08 mmol) in 20 ml of DMF is added drop-wise, and the resulting solution is stirred overnight at room temperature. The pH of the mixture is then adjusted to 6-7 by the addition of 1 N HC1, and the product is partitioned between H2O and EtOAc. The aqueous phase is extracted again with EtOAc, and the combined organic phases are washed with water and brine, dried over magnesium sulfate, and concentrated to a crude residue, which is purified on a silica gel column, eluting with 25% EtOAc in hexane to obtain 7.52 g (23.54 mmol ; 50%) of the product as an oil.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Hydroxyethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARTESIAN THERAPEUTICS, INC.; WO2005/16885; (2005); A2;,
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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

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 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;,
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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H7NO2

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 102359-00-2, 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. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, 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.

1-[5-(Morpholine-4-carbonyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), morpholine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(morpholine-4-carbonyl)-1,3-dihydro-indol-2-one. 1NMR (300 MHz, DMSO-d6) delta 10.54 (br s, 1H, NH), 7.24 (m, 2H), 6.83 (d, J=7.6 Hz, 1H), 3.56 (m, 4H, 2*CH2), 3.49 (s, 2H, CH2), 3.47 (m, 4H, 2*CH2). MS APCI neg. m/z 245 [M+-1].

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

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. Application In Synthesis of 7-Chloroisatin

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. COA of Formula: C10H9NO2

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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. 193354-13-1, name is 5-Iodoindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6INO

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

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; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 5-Methylindolin-2-one

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized from methanol or acetone to give compound (1-19).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3484-35-3, its application will become more common.

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H9NO3

To a reaction vessel were added (R)-glycidylphthalimide 4.06 g (20.0 mmol) obtained above, 4-chloro-2-methoxyphenol 3.17 g (20.0 mmol), cesium fluoride 0.608 g (4.0 mmol) and DMF 30 mL, and the mixture was stirred at 80 C. for 38 hours. After evaporation of the solvent, to the condensed residue was added 1,2-dichloroethane and the mixture was washed with an aqueous 3% NaOH solution, an aqueous 1% HCl solution and an aqueous 3% NaCl solution successively. The organic layer was taken and evaporated to give crude (R)-1-(4-chloro-2-methoxyphenoxy)-3-phthalimido-2-propanol 6.21 g (yield 87%, chemical purity 96%) as a pale yellow solid. 1HNMR (CDCl3, 270 MHz) delta3.17 (br, 1H), 3.80 (s, 3H), 3.88-4.11 (m, 4H), 4.23-4.32 (m, 1H), 6.83-6.86 (m, 3H), 7.71-7.88 (m, 4H) 13CNMR (CDCl3, 68 MHz) 640.9, 55.9, 68.5, 72.5, 112.4, 116.0, 120.3, 123.2, 126.9, 131.8, 133.9, 146.6, 150.3, 168.3

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Miki, Yasushi; Mikami, Masafumi; US2006/19993; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Nitrophthalimide

General procedure: To a solution of benzazoles (0.05 mol) in ethanol, formaldehyde (aq. 37% solution, 0.5 ml) and 4-(4-nitrobenzyloxy)-aniline 2 were added with vigorous stirring and heated on a water bath for 5 min and left at room temp for overnight. The solid so obtained was washed with methanol and recrystallized from suitable solvent.

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rastogi, Nisheeth; Kant, Padam; Indian Journal of Heterocyclic Chemistry; vol. 24; 1; (2014); p. 77 – 80;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem