July 2021 - Page 24 of 49 - Indolines-derivatives

Brief introduction of 101207-45-8

These common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-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. COA of Formula: C16H13NO2

Synthesis intermediate 4. Dissolve 12.3g of 2- (4-methylbenzyl) -1H-isoindole-1,3-dione in chloroform, then add 8.7g of chlorosulfonic acid, and react at 80 C for 3h After completion, 15.75 g of Intermediate 4 was obtained after washing with water and removing the solvent, and the yield was 95%.

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

Reference:
Patent; Zhengzhou Shouxing Pharmaceutical Institute Co., Ltd.; Deng Zhaoxi; (13 pag.)CN110483497; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A new synthetic route of 317-20-4

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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Fluoroisatin

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.

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 317-20-4.

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

New downstream synthetic route of 1127-59-9

Reference of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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.

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25percent, 421 mg, 3.0 mmol) and H2O2 (30percent, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 °C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30percent NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89percent yield).

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; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Extended knowledge of C8H4BrNO2

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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

Example 38Preparation of ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate (BI24) Step 1. 5-Bromo-3-hydroxyisoindoline-1-one (BI25); A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C. for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

Reference:
Patent; Hunter, James E.; Lo, William C.; Watson, Gerald B.; Patny, Akshay; Gustafson, Gary D.; Pernich, Dan; Brewster, William K.; Camper, Debra L.; Lorsbach, Beth; Loso, Michael R.; Sparks, Thomas C.; Joshi, Hemant; Mandaleswaran, Adiraj; Sanam, Ramadevi; Gundla, Rambabu; Iyer, Pravin S.; US2012/329649; (2012); A1;,
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Indoline | C8H9N – PubChem

Continuously updated synthesis method about 39603-24-2

Application of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of phenylhydrazine (1 mmol), 3-aminocrotononitrile (1 mmol), and InCl3 (0.1 mmol) in water (10 ml) was added to isatin (1 mmol) and the reaction mixture heated under reflux at 100 C for 10 min. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature; the precipitate was filtered off and washed with methanol to obtain pure 13 as a colorless solid. Spectroscopic data for all the compounds are given below.

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Balamurugan, Kamaraj; Perumal, Subbu; Menendez, J. Carlos; Tetrahedron; vol. 67; 18; (2011); p. 3201 – 3208;,
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Introduction of a new synthetic route about 32692-19-6

Related Products of 32692-19-6, 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 32692-19-6 as follows.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Sources of common compounds: 32692-19-6

Reference of 32692-19-6, 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 32692-19-6 as follows.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Discovery of 2518-24-3

Related Products of 2518-24-3, A common heterocyclic compound, 2518-24-3, name is 4-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

4-Aminoisoindoline-1,3-dione (2, 2.00 g, 12.3 mmol) was dissolved in MeOH(200 mL), and the solution was treated with N-bromosuccinimide (2.19 g,12.3 mmol). The reaction was stirred at room temperature for 50 min. The solid thatprecipitated was collected by filtration and washed with MeOH to give bromide 3(2.21 g, 9.21 mmol, 75%) as a yellow powder, mp 287-289C. 1H NMR (DMSOd6):d 11.1 (s, 1H), 7.51 (d, J D 8.9 Hz, 1H), 6.90 (d, J D 8.9 Hz, 1H), 6.53 (br s,2H); 13C NMR (DMSO-d6): d 170.0, 167.7, 146.5, 139.6, 130.2, 123.6, 112.4, 101.6;MS: m/z 240, 242 (C8H5BrN2O2, MC¢, ca. 1:1).Anal. Calcd for C8H5BrN2O2: C, 42.51; H, 1.78; N, 6.20. Found: C, 42.63; H, 1.86;N, 6.14.

Reference:
Article; Gnanasekaran, Krishna Kumar; Rivera, Mario; Bunce, Richard A.; Organic Preparations and Procedures International; vol. 50; 3; (2018); p. 372 – 374;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Extended knowledge of C11H9NO3

Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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. Formula: C11H9NO3

In a 10 ml reaction tube, adding phosphine nitrogen ligand L10a (0.35 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laq (40.6 mg, 0.2 mmol) with anhydrous sodium carbonate (2.12 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 aq. The conversion is 100%, enantiomeric excess is 92%. 2 Aq: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2436-29-5, its application will become more common.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

New learning discoveries about 7477-63-6

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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., 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.

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 7477-63-6.