Category: 18711-13-2

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-2,3-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 18711-13-2, category: indolines-derivatives

4,7-Dichloro-3-(2-(4-cyclopropyl-2-fluorophenyl)-2-oxoethyl)-3-hydroxyindolin-2- one (EXAMPLE 18): To 4,7-dichloroindoline-2,3-dione (A) ( 261 mg, 1.21 mmol) in 15 mL of methanol were l-(4-cyclopropyl-2-fluorophenyl)ethanone (B) (280 mg, 1.57 mmol) and 10 drops of diethylamine (2). The reaction was stirred at 50C for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CH2C12) to get an off white solid. 4,7-Dichloro-3-(2-(4-cyclopropyl-2-fluorophenyl)-2-oxoethyl)-3- hydroxyindolin-2-one (EXAMPLE 18): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 0.82 (m, 2H), 1.07 (m, 2H), 2.01(m, 1H), 3.66 (d, 1H, J=16 Hz), 4.26 (d, 1H, J=16Hz), 6.44(s, 1H), 6.91(d, 1H, J=8Hz), 7.01 (m, 2H), 7.31 (d, 1H, J=8Hz), 7.57(m, 1H), 10.96 (s, 1H). Chiral separation was performed by a method substantially similar to the method described above. LC screening was performed with: column: RegisCell, 250 mm x 4.6 mm, 5 mum, hexane/IPA (80/20), 1.5 ml/min, injection volume: 2.0 mu, pressure: 51.5 bar. Peak 1 : retention time: 5.16 min, width: 0.238 min, area: 3716.20, area %: 49.78. Peak 2: retention time: 6.49 min, width: 0.324 min, area: 3749.55, area %: 50.22.

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; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H3Cl2NO2

General procedure: A solution of C3-beta-cholestrylcarboxylate (4) (1 mmol), proline (11)(1 mmol) and isatin (1a-f)/acenaphthenequinone (7)/ninhydrin (9)(1 mmol) was stirred in aqueous methanol for 1-2 h at reflux temperature.After the completion of reaction as indicated by TLC, methanolwas evaporated under reduced pressure. The crude product waspurified by column chromatography using hexane:EtOAc mixture (2:1)as an eluent.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Periyasami, Govindasami; Kamalraj, Subban; Padmanaban, Ramanathan; Yeswanth Kumar, Santhakumar; Stalin, Antony; Arumugam, Natarajan; Suresh Kumar, Raju; Rahaman, Mostafizur; Durairaju, Periyan; Alrehaili, Abdulaziz; Aldalbahi, Ali; Bioorganic Chemistry; vol. 88; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 18711-13-2, 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. 18711-13-2 name is 4,7-Dichloroindoline-2,3-dione, 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.

General procedure: A mixture of isatin (1a) (0.3 gm, 2.0 mmol) and enaminone (2a) (0.333 gm,2.4 mmol) in 10 mL of water was heated in an oil bath at 80C for 9 hours. Initially,orange-colored reaction mixture appeared to be homogeneous but with the progress ofthe reaction, yellow color solid precipitated out. After the TLC indicated the completeconsumption of starting materials, the precipitated solid was filtered off. The solid wasthen dried under vacuum and purified by silica gel column chromatography by using EA: hexane (8:2) as an eluent to provide the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,7-Dichloroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Tiwari, Keshri Nath; Thakar, Snehal Rajendra; Kumar, Vaneet; Prabhakaran; Synthetic Communications; vol. 48; 23; (2018); p. 2965 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 18711-13-2,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.

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 C and stirred for additional 3-3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 ¡Á 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1-1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 18711-13-2, 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6-10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Saffron solid, yield: 76%, m. p.: 151.8-153.3C, Rf=0.52 (petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.51 (d, J=8.7Hz, 1H), 7.10 (d, J=8.7Hz, 1H), 4.94 (d, J=2.4Hz, 2H), 2.34 (t, J=2.4Hz, 1H).13C NMR (100MHz, CDCl3) delta 178.68, 157.00, 146.19, 140.48, 133.05, 126.79, 117.16, 116.11, 77.22, 73.27, 31.94

The chemical industry reduces the impact on the environment during synthesis 4,7-Dichloroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-2,3-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 18711-13-2, Computed Properties of C8H3Cl2NO2

General procedure: To a stirred solution of ethyl 2-(triphenylphosphoranylidene)acetate (3.83 g, 11.0 mmol) in CH2Cl2 (30.0 mL) was added isatin (1.47 g, 10.0 mmol) at 0 C. After stirring for 8 h at 0 C, the mixture was concentrated by rotary evaporation. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=3:1-10:1) to afford the compound 1a as a red solid (1.78 g, 82 %).

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; Zhao, Jia; Guan, Shuicheng; Zhou, Xiaojian; Han, Wenyong; Cui, Baodong; Chen, Yongzheng; Tetrahedron; vol. 72; 22; (2016); p. 3098 – 3104;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 18711-13-2, 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 18711-13-2 as follows.

General procedure: Example 1- Synthesi s of 4,7 dichloroisatin analogs [0176] An appropriate acetophenone and 4, 7-dichloroisat were condensed in the presence of a catalytic amount of diethylamme to prepare the desired compound in quantitative yield. Example compounds: R1 = 4′-CN (PT-1-11); 2′-GCH3 (PT-1-12) ; 3′- OCH3 (PT-1 -18) ; 2 FontWeight=”Bold” FontSize=”10″ ,4′-OCH3 (PT-1-19); 2,.3′-( }( 1 i ¡¤. (PT-1-20); 3′,4OCH3 (PT-1 -21 ); 35’OCH3 (PT-1-22); 2,,3′,4′,-OCH3 (PT-1-23); 3’A 5′-OCH3 (PT-1-13); 4′-OC2H5 (PT-1- 14); 4 -CF3 (PT-1-15); 4′-OCF3 (PT-1-16); 4′-N(CH3)2 (PT-1-17); 4′-OPh (PT-1-60); 4′-SCH3 (PT-1-67); and 4′-C(CH3)2 (PT-1-67).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGETOWN UNIVERSITY; TORETSKY, Jeffrey, A.; UREN, Aykut; WO2015/61229; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 18711-13-2,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.

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 18711-13-2,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.

Example 1- Synthesis of 4,7 dichloroisatin analogs [0143] An appropriate acetophenone and 4, 7-dichloroisatin were condensed in the presence of a catalytic amount of diethylamine to prepare the desired compound in quantitative yield. Example compounds: R1 = 4′-CN (PT-1-11); 2′-OCH3 (PT-1-12) ; 3*-OCH3 (PT-1-18) ; 2′,4′-OCH3 (PT-1-19); 2′,3*-OCH3 (PT-1-20); 3*,4OCH3 (PT-1-21); 3*,5*OCH3 (PT-1-22); 2′,3*,4′,-OCH3 (PT-1-23); 3*,4′,5*-OCH3 (PT-1-13); 4′-OC2H5 (PT-1-14); 4′-CF3 (PT-1-15); 4′- OCF3 (PT-1-16); 4′-N(CH3)2 (PT-1-17); 4′-OPh (PT-1-60); 4′-SCH3 (PT-1-67); and 4′-C(CH3)2 (PT-1-67).

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GEORGETOWN UNIVERSITY; TORETSKY, Jeffrey, A.; BROWN, Milton, Lang; TOSSO, Perrer, N.; UREN, Aykut; KONG, Yali; WO2013/155341; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 18711-13-2, These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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.

3-(2-(4-(Aziridin-l-yl)phenyl)-2-oxoethyl)-4,7-dichloro-3-hydroxyindolin-2-one (EXAMPLE 2): To 4,7-dichloroindoline-2,3-dione (A) (300 mg, 1.39 mmol) in 15 mL of methanol were l-(4-(aziridin-l-yl)phenyl)ethanone (B) (0.9 g, 5.5 mmol) and 10 drops of diethylamine (2). The reaction was stirred at 50C for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CH2C12) to get an off white solid. 3-(2-(4-(Aziridin-l-yl)phenyl)-2-oxoethyl)-4,7-dichloro-3-hydroxyindolin-2-one (EXAMPLE 2): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 2.16 (s, 4H), 3.64 (d, 1H, J=16 Hz), 4.32 (d, 1H, J=16Hz), 6.41(s, 1H), 6.89(d, 1H, J=8Hz), 7.05 (d, 2H, J=8Hz), 7.30 (d, 1H, J=8Hz), 7.80 (d, 2H, J=8Hz), 10.95 (s, 1H).

Statistics shows that 4,7-Dichloroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 18711-13-2.

Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem