Category: 39755-95-8

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 39755-95-8 as follows. Safety of 5-Methoxyisatin

5-Hydroxy isatin (2). To a stirred solution of 5-methoxy isatin (1) (10.0 g, 56.5 rnmol, 1.0 equiv) in CH2CI2 (40 mL) at 0 C, BBr3 (36.8 g, 147 mmol, 2.6 equiv) was added dropwise over 2 h under vigorous stirring at 0 C. Upon completion of addition, the ice bath was removed and the reaction mixture was stirred for another 1 h at room temperature and was diluted with CH2CI2 (500 mL), cooled to 0 C, quenched by careful sequential addition of solid NaHC03 (37 g), and cold (0-5 C) H20 (60 mL) (CA UTION, HBr gas). The resulting mixture was washed with brine (50 mL), and the combined aqueous phases were extracted with CH2CI2 (50 mL). The combined organic phases were concentrated and the residue was recrystalhzed from glacial acetic acid to yield isatin 2 as a dark red solid (8.8 g, 54 mmol, 95% yield). R = 0.31 (silica gel, CH2Cl2:EtOAc 1 : 1); IR (film) vmax = 3278, 1720, 1614, 1477, 1291, 1194, 881, 822, 800 cm”1; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, DMSO): delta = 10.73 (s, 1 H), 9.52 (br, 1 H), 7.00 (dd, J = 8.5, 2.6 Hz, 1 H), 6.83 (d, J = 2.6 Hz, 1 H), 6.74 (d, J = 8.3 Hz, 1 H) ppm; 1 C NMR (125 MHz, CDC13): delta = 184.9, 159.5, 153.2, 143.1, 125.1, 118.2, 113.1, 110.5, 105.1 ppm; HRMS (ESI-TOF): calcd for C8H6N03+ [M+H+] : 164.0342, found 164.0344.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WILLIAM MARSH RICE UNIVERSITY; BRISTOL-MYERS SQUIBB COMPANY; THE SCRIPPS RESEARCH INSTITUTE; NICOLAOU, Kyriacos, C.; LU, Min; MANDAL, Debashis; GANGWAR, Sanjeev; CHOWDARI, Naidu, S.; POUDEL, Yam, B.; WO2015/23879; (2015); A1;,
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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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Methoxyisatin

Preparation of 5-methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)-indole-3-carbaldehyde; 5-Methoxy isatin (0.2 g, 1.1 mmol, 1 eq.) was dissolved in hydrazine hydrate (1.2 ml_, 38 mmol, 34 eq.) and refluxed for 15 minutes. The reaction mixture was poured into cold water and extracted with EtOAc. The combined organic extracts were dried on Na2SO4. The solvent was evaporated to afford crude 5-methoxy-1 ,3-dihydro-indol-2-one that was purified by silica gel column chromatography (eluent: hexane/EtOAc from 10:0 to 6:4). Yield: 27%. MS (m/z): 164.2 (MH+).Phosphorous oxybromide (0.35 ml_, 3.1 mmol, 2.5 eq.) was added drop wise to a solution of DMF (0.3 ml_, 3.7 mmol, 3 eq.) in dry methylene chloride at 00C. The mixture was stirred at 00C for 30 minutes, then a solution of 5-methoxy-1 ,3-dihydro-indol-2-one (0.2 g, 1.2 mmol, 1 eq.) in dry methylene chloride (2 ml_) was added and the mixture was refluxed for 3 hours. The solution was neutralized with solid NaHCO3 and extracted with methylene chloride. The organic layer was dried on Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by silica gel column chromatography (eluent: hexane/AcOEt 6:4 to 4:6) to give pure 2-bromo-5-methoxy-indole-3-carbaldehyde. Yield: 45%. MS (m/z): 254.1 (MH+). A stirred solution of 2-bromo-5-methoxy-indole-3-carbaldehyde (2.0 g, 7.9 mmol, 1 eq.) in DME (2 ml_) was deoxygenated by bubbling argon for 10 minutes at rt. Pd(PPh3)4 (0.9 g, 0.8 mmol, 0.1 eq.) was added followed by a solution of 1-methyl-4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazole (2.4 g, 1 1.63 mmol, 1.48 eq.) in ethanol (2.5 ml_). 2M Na2CO3 (33 ml_, 8.5 eq.) was also deoxygenated with argon and added. The resulting mixture was heated at 78C for 18 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted with methylene chloride. Organic layer was dried on anhydrous Na2SO4 and evaporated under reduced pressure to give the crude product 1f. Yield: 89%. MS (m/z): 256.1 (MH+).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.; WO2010/30727; (2010); A1;,
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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., 39755-95-8

To a suspension of 5-methoxyindoline-2,3-dione (250 mg, 1.41 mmol) in ethylene glycol (1mL) were added hydrazine monohydrate (140 mL) and KOH (79 mg, 1.41 mmol). The mixture was heated under microwave irradiation at 140 C for 5 minutes. Water was added and the mixture was neutralized with 1N HCl. The obtained suspension was extracted 3 times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuum to give 186 mg (81%) as a yellow solid and was used for the next step without further structure determination.

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Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
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39755-95-8, Name is 5-Methoxyisatin, 39755-95-8, 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.

5-Methoxyisatin (2.00 g, 11.2 mmol) was dissolved into 47% hydrobromic acid (20 mL) and refluxed at 150 C for 3 h. The solution was diluted with water (100 mL) and extracted by ethyl acetate (300 mL ¡Á 5). The organic layers were combined and dried with anhydrous sodium sulfate. After concentration in vacuo, the crude dark-brown solid (1.64 g, 89% yield) was obtained. In the subsequent synthesis, 5-hydroxyisatin was used without further purification. 1H NMR (CD3OD, 500MHz) delta 6.78 (d, 1H, J=8.3Hz, H-7), 6.94 (d, 1H, J=2.4Hz, H-4), 7.02 (dd, 1H, J=8.3, 2.4Hz, H-6).

Statistics shows that 5-Methoxyisatin is playing an increasingly important role. we look forward to future research findings about 39755-95-8.

Reference:
Article; Yasuda, Daisuke; Takahashi, Kyoko; Ohe, Tomoyuki; Nakamura, Shigeo; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7709 – 7714;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39755-95-8, 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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of acetophenone or isatin (5 mmol) in THF (10 mL), BF3¡¤OEt2 (7.5 mmol) was added at 0C under the atmosphere of N2 and the mixture was stirred for 10 minutes. To the cooled mixture, anhydrous hydrazine (7.5 mmol) was added in one portion and the reaction mixture was stirred at 0C under the atmosphere of N2 for 30 min. The reaction was quenched by the addition of a saturated solution of NH4Cl (4 mL), extracted by ethyl acetate (3 ¡Á 15 mL) and purified by column chromatography (ethyl acetate-CH2Cl2; 3 : 7) to afford hydrazones 2-22.

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:
Article; El-Azab; Ghabbour; El-Husseiny; Maarouf; Mohamed; Abdel-Aziz; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2837 – 2844; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2837 – 2844,8;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 39755-95-8 as follows. 39755-95-8

General procedure: The preparation was divided into two steps. Firstly, substituent indoline-2,3-dione (1 equiv) was dissolved in ethanol (10 mL), hydrazine hydrate (2 mL) was added. The reaction mixture was refluxed with magnetic stirring for 3 h and cooled to 0 C, then sodium hydroxide (3 equiv) was added, refluxed for 0.5 h and cooled to room temperature, then 150 mL water was added. The mixture was acidified by adding 2 N hydrochloric acid to pH 2, and extracted twice with dichloromethane. The organic filtrate was washed twice with brine, dried (Na2SO4), and then concentrated to give corresponding indolin-2-one by high-vacuum drying. Secondly, a mixture of the corresponding indolin-2-one (1 equiv) and furan-2-carbaldehyde (1 equiv) in ethanol was added two drops of piperidine and refluxed with magnetic stirring for 5 h. After the mixture cooled, the precipitate was filtered, washed with cold ethanol, dried, and recrystallized from methanol to afford the terminal product.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhong, Ye; Xue, Mengzhu; Zhao, Xue; Yuan, Jun; Liu, Xiaofeng; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Xu, Yufang; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1724 – 1734;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 39755-95-8, name is 5-Methoxyisatin, 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 39755-95-8. 39755-95-8

Synthesis of l -Benzyl-5-methoxyindolin-2-one[00143] A stirred solution of 5-methoxyisatin (5.0 g, 28 mmol) in dry DMF (40 mL) was cooled in an ice bath before addition of sodium hydride (60 wt% in mineral oil, 1.7 g, 42 mmol) slowly, the dark red solution turning quickly black. After stirring for 20 min, BnBr (3.7 mL, 31 mmol) was added to the reaction mixture by syringe and the resulting mixture was stirred for 1 h. Water (150 mL) was added with stirring, and the resulting dark red precipitate collected by filtration and washed with water to give l-benzyl-5- methoxyindoline-2,3-dione as a dark red solid (6.1 g, 81%). NMR (400 MHz, CDC13) delta 7.39-7.31 (m, 5H), 7.17 (s, 1H), 7.03 (d, J = 8.1 Hz, 1H), 6.68 (d, J = 8.6 Hz, 1H), 4.92 (s, 2H), 3.79 (s, 3H). MS ESI 268.1 [M + H]+, calcd for [C16H13N03+ Hf 268.09.

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 5-Methoxyisatin.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
Indoline – Wikipedia,
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