Author: Jessica.F

These common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-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. Application In Synthesis of 5-Chloro-7-methylindoline-2,3-dione

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..

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

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;,
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Related Products of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5b): Melting point 247-249 C; white solid, 96%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.82 (d, J = 13.96 Hz, 1H), 4.58-4.61 (m, 1H), 4.49 (d, J = 10.24 Hz, 1H), 3.79 (d, J = 13.2 Hz, 1H), 3.60 (d, J = 16.82 Hz, 1H), 3.39 (d, J = 5.4 Hz, 1H), 2.94 (d, J = 13.96 Hz, 1H), 2.71-2.77 (m, 1H), 2.41 (d, J = 13.92 Hz, 1H), 6.56-6.61 (m, 2H), 6.98-7.65 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 40.6, 47.4, 52.7, 53.2, 61.3, 67.2, 70.9, 100.8, 110.1, 121.9, 122.4, 122.5, 123.8, 124.5, 126.4, 126.5, 127.2, 128.3, 128.4, 128.5, 128.6, 128.7, 128.9, 129.1, 131.4, 131.6, 131.8, 133.2, 136.3, 138.2, 138.5, 138.6, 144.6, 179.5, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.85; H, 3.83; N, 4.72.

The chemical industry reduces the impact on the environment during synthesis 5-(Trifluoromethoxy)indoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6341-92-0, name is 6-Chloroisatin, 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. category: indolines-derivatives

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196-198 C.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4721712; (1988); A;,
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Synthetic Route of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

General procedure: A mixture of 2-(7-methoxynaphthalen-1-yl)ethanamine (compound 3, 101 mg, 0.5 mmol), sodium acetate (82 mg, 1.0 mmol) and cyclic anhydrides 1.0 mmol) in 5mL acetic acid was heated to reflux for 3 h in a round bottomed flask. After the completion of reaction (as evidenced by TLC), the resulting mixture was concentrated under reduced pressure and washed with ethyl acetate (10 mL×3), then the concentrated organic layer was purified by column chromatography on silica gel to obtain pure product.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Ying; Pi, Weiyi; Ang, Wei; Liu, Yuanyuan; Li, Chunlong; Zheng, Jiajia; Xiong, Li; Yang, Tao; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1672 – 1676;,
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Related Products of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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 7-fluoroindoline-2,3-dione (500 mg, 3.03 mmol) in DMF (5 mL) were successively added K2C03 (502 mg, 3.63 mmol) and methyl iodide (0.199 mL, 3.18 mmol). The resulting mixture was stirred at RT for 1 hr. The mixture was quenched with water, diluted with EtOAc and saturated aqueous NaHC03 solution and both phases were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure to afford the title product (497 mg, 2.219 mmol, 73.3% yield) as yellow solid. Rt = 0.69 min (UPLC-MS); ESI-MS = 179.9 [M+1]+ (UPLC-MS).

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

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-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 667463-64-1, SDS of cas: 667463-64-1

General procedure: Unless indicated otherwise, a solution of 2-aminobenzamide 1 (0.1 mmol), isatin 2 (0.1 mmol), the catalyst 4e (0.02 mmol), and 5 A molecular sieves (30 mg) in 1,2-dichloroethane (2 mL) was stirred at 70 C for 12 h. Next, the reaction mixture was diluted with acetone, which was then filtered to remove molecular sieves and the solid powder was washed with acetone. The resultant solution was condensed by evaporation under reduced pressure, which was further purified through preparative thin layer chromatography on silica gel to yield pure products 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Yan; Liu, Yan; Tu, Shu-Jiang; Shi, Feng; Tetrahedron Asymmetry; vol. 24; 20; (2013); p. 1286 – 1296;,
Indoline – Wikipedia,
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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. 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. category: indolines-derivatives

General procedure: Procedure M2. A mixture of the appropriate 2-(bromoalkyl)-isoindoline-1,3-dione (1 equiv)with 1,2,3,4-tetrahydoisoquinoline (1 equiv) in the presence of K2CO3 (2.5-3 equiv) was stirred inacetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under vacuum, producinga residue which was further dissolved in 40 mL of sodium bicarbonate and extracted with ethyl acetate(3 x 30 mL). The organic layer was acidified 2 M HCl and extracted with distilled water (3 x 30 mL).Then, the combined aqueous extracts were alkalized using 4M NaOH, extracted with DCM and driedwith anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gelcolumn chromatography (S4) yielding a yellow oil. The final product was obtained in the form ofhydrochloride salt. The following compounds were obtained.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-79-5, These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-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.

General procedure: To a suspension of 5-nitro-3-substituted-2-oxindole derivatives 8-12 or commercially available 5-nitroindolin-2-one (1 mmol) in amixture of ethanol and water (10 mL, 4:1 v/v) was added iron powder (560 mg.10 mmol,10 equiv.) and NH4Cl (134 mg, 2.5 mmol,2.5 equiv.). The mixture was refluxed for 2 h, cooled and filteredthrough Celite. The filtrate was diluted with water (5 mL) andextracted with dichloromethane (3 x 10 mL). The combinedorganic layers were washed with water (10 mL) and brine (10 mL),dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by crystallization withethyl ether.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romagnoli, Romeo; Baraldi, Pier Giovanni; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Salvador, Maria Kimatrai; Lopez-Cara, Luisa Carlota; Bortolozzi, Roberta; Mattiuzzo, Elena; Basso, Giuseppe; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 258 – 270;,
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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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6-Fluoroindoline-2,3-dione

Add 11.33g NaNO3 and 100mL H2SO4 to a 500mL reaction flask.With stirring, the temperature of the ice bath was lowered to 0 C. Take 20.00g of compound 1-1,Dissolved in 120mL H2SO4,Slowly add the 1-1 H2SO4 solution to the reaction flask,After dripping, the reaction was held at 0 C for 1 hour, and then the reaction solution was poured into 1 L of ice water.After stirring for 0.5 hours, it was filtered and the filter cake was washed with water until neutral.The filter cake was washed with 80 mL of EtOH / H2O (7: 3) for 0.5 hours, filtered,The filter cake was dried to obtain 18.83 g of a crude product of 2-1.Yield: 74%.

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 324-03-8.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Ma Dawei; Wang Kailiang; Xia Shanghua; Li Zheng; Zhao Jinlong; Li Ying; (82 pag.)CN110642874; (2020); A;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 169037-23-4

Preparation of 3-hydroxy-5-trifluoromethoxy-3-(nitromethyl)indolin-2-one 5-trifluoromethoxy isatin ((0.115 g) and nitromethane (0.1 ml) were added to water and the reaction mixture was vigorously stirred at a temperature of 30 C. for 20 minutes. The obtained product was extracted with ethyl acetate and the solvent was removed to give pure product.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAO, Mandapati Mohan; PRATHIMA, Parvathaneni Sai; US2013/345438; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem