Tag: M.W=100-200

These common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-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. Recommanded Product: 2-Methylisoindoline-1,3-dione

General procedure: To N-methylphthalimide (1a) (8 mmol), N-benzylphthalimide (1e) (8 mmol) or appropriate compound 2b-d(8 mmol) stirred in acetic acid (25 mL) tin granular (1.90 g, 16 mmol) and hydrochloric acid (10 mL, d25 = 1.2 g/mL) were added. The whole lotwas heated to reflux for 3 h. The solvents were removed under reduced pressure and to the residue were added ethyl acetate (50 mL) and sodium carbonate solution(10% in water) to obtain an alkaline environment. Then the organic layer was separated, washed with water, dried with magnesium sulfate(VI) and evaporated to give the crude products 3. Thecompounds 3 were purified by crystallization.

The synthetic route of 2-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jo?wiak, Andrzej; Zagorski, Piotr M.; P?otka, Mieczys?aw W.; Cal, Dariusz; Tetrahedron Letters; vol. 55; 15; (2014); p. 2420 – 2422;,
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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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 64483-69-8

PREPARATION V 1-(N-Benzoylcarbamoyl)-5-acetyloxindole To 3.0 g. (.017 mole) of 5-acetyloxindole in 75 ml. of xylene and 25 ml. of toluene was added 3.3 g. (.022 mole) of benzoylisocyanate, and the reaction mixture heated to reflux overnight. The hot suspension was filtered, washed with toluene and air dried, 4.4 g., m.p. 232C. dec.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; EP208510; (1991); B1;,
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Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, 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 1504-06-9, category: indolines-derivatives

Step 1 : Preparation of 3-methyl-5-(3-trifluoromethylphenyl)- 1 ,3-dihydroindol-2-oneA solution of 3-methyloxindole (5.06 g, 34.4 mmol) in iV,iV-dimethylformamide (60 mL) was cooled to 0 0C. N-Bromosuccinimide (6.23 g, 35.0 mmol) was added, and the resulting solution was stirred for 18 hours while slowly warming to room temperature. The reaction was then diluted with ethyl acetate (100 mL) and washed with 1 :1 saturated aqueous NaCl solutuion:H2O (3 x 75 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid that was used without further purification in the next step described below.A mixture of the crude product described above (1.02 g5 4.51 mmol), 3- (trifluoromethyl)phenylboronic acid (0.983 g, 5.18 mmol), sodium carbonate (0.884 g, 8.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.252 g, 0.218 mmol) in ethylene glyclol dimethyl ether (8.0 mL) and H2O (1.0 mL) was warmed to 80 0C. After 20 hours, the mixture was cooled to room temperature, poured into 1 : 1 saturated aqueous NaCl solution:H2O (50 mL), and extracted with ethyl acetate (3 x 50 mL). The organic extracts were combined, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 10-35% ethyl acetate/hexanes, to give 3-methyl-5-(3-trifluoromethylphenyl)-l,3-dihydroindol-2-one as a white solid.1H NMR (CDCl3): delta 8.27 (br s, 1 H), 7.79 (s, 1 H), 7.72 (d, I H1 J = 7.3 Hz), 7.56 (m, 2 H), 7.46 (m, 2 H), 6.99 (m, 1 H), 3.55 (dd, 1 H, J = 15.3, 7.8 Hz), 1.57 (d, 3 H, J = 7.7 Hz) MS: m/e 292.41 (M + H)+

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

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
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1504-06-9, name is 3-Methyloxindole, 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. SDS of cas: 1504-06-9

A magnetic stirrer was added to the Schlenk tube-sealed reactor, and the 2- oxindole compound of formula II-1 (0.3 mmol) was added, followed by the addition of Cu (OAc) 2 (0.03 mmol) and di-tert-butyl peroxide. (0.6mmol); The reactor was then placed in an oil bath equipped with magnetic stirring, and the reaction was heated and stirred at 120 C for 4 hours. The reaction mixture was completely monitored by TLC. After the completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue was separated by column chromatography (eluent solvent: ethyl acetate / n-hexane) to obtain he title compound formula I-1 , yield 80%.

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (11 pag.)CN108129378; (2018); A;,
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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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 317-20-4

General procedure: The mixture of isatin 1 (58.9 mg, 0.4 mmol), antipyrine 2 (37.6 mg, 0.2 mmol) andimidazole (20 mol %, 0.04 mmol) in 1 mL H2O were stirred at 80 . Once thereaction completed, the solid mixture was filtered, washed by water and dried undervacuum to afford the analytically pure products 3. In some cases, the desired pureproducts were obtained by silica gel chromatography using ethyl acetate as eluent.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Computed Properties of C8H8N2O2

General procedure: A solution of indoline (20) (1.88 mL, 16.78 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (22) (3.73 g, 20.13 mmol) in dry methanol (20 mL) was treated with AcOH (2.37 mL, 41.95 mmol) followed by NaCNBH3 (1.26 g, 20.13 mmol) at 0 C. ;The reaction was brought to room temperature and stirred for 3 h. ;The reaction was basified with 1 N NaOH solution and product was extracted into CH2Cl2. ;The combined CH2Cl2 layer was dried (Na2SO4) and solvent was evaporated to obtain crude product. ;The crude was purified by column chromatography (EtOAc:hexanes, 1:9) to obtain the title compound

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; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
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Reference of 86626-38-2, 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. 86626-38-2 name is 4-Bromoindoline, 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.

Obtained above in MeCN (8mL) 4- bromo-indoline (759mg, 3.81mmol) and the mixture of (Boc) 2O (976mg, 4.48mmol) was stirred at room temperature overnight. After evaporation, the residue was dissolved in ethyl acetate (40 mL), washed with water (3 ¡Á 20 mL) and brine (1x20mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 as a white solid (840 mg, 74%).

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

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
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Reference of 74572-29-5, 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 74572-29-5 as follows.

A suspension of copper (I) iodide (88 mg, 0.46 mmol), l-(3-bromophenyl)ethan-l-ol (1.85 g, 9.19 mmol) potassium carbonate (0.65 g, 4.59 mmol) and 5-chloroisoindolin-l-one (0.77 g, 4.59 mmol) in anhydrous A’ A’-d i m e th y 1 fo rm am i dc (3.8 mL) was purged with nitrogen and heated at 150 C for 16 h. The mixture was diluted with 10% ammonium hydroxide solution. General Work-up Procedure 1 was followed. The residue was purified on silica gel (ethyl acetate in hexanes 40% isocratic) to give the title compound as an off-white solid. Yield: 0.42 g (32%).

According to the analysis of related databases, 74572-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
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3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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. Recommanded Product: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

a synthetic process of amlodipine besylate,The difference from Embodiment 1 is thatStep 2 specifically includes:In the reaction tank,Put 350kg of toluene,Stirring,Distilling toluene,After the liquid in the water separator is full,Keep the reflux water for 60 minutes,Sampling to determine water separation,When the water content of the reflux liquid is ?0.2%,Change the reflux to distillation,Distilling off toluene,Stir and cool down,When the temperature inside the tank drops to 45 C,Filling the reaction tank with nitrogen,Continue to cool down to 5 C,40 kg of N-(2-hydroxyethyl)-phthalimide was added with stirring.Then add 20kg of sodium hydride,Plus,Close the lid,Stir at 5 C,38.4 kg of ethyl 4-chloroacetoacetate was taken in the measuring tank.45kg of toluene and mix well,Drop into the reaction tank at 5 CAdd a solution of ethyl 4-chloroacetoacetate in toluene,The dripping time is controlled at 4 hours.Plus,Continue to stir the reaction for 2 hours.Slowly warming up,The temperature of the reaction solution was slowly raised to 38 C within 5 hours.The reaction time is more than 12 hours.Warm up to 51 C and keep warm for 1 hour.Until the reaction is complete,Cooling down,Control the internal temperature of 35 C,Add 61kg glacial acetic acid,Plus,Stirring was continued for 60 minutes to stir the material in the reaction solution evenly.The internal temperature is controlled at 35 C.Add 180kg of water,Plus,Continue to stir for 30 minutes.Stop filling with nitrogen,Stop stirring,Stand still and separate the water layer into the bucket.Transfer the toluene layer to the washing tank,Transfer the water layer to the reaction tank,Add 75 kg of toluene to the reaction tank.Stir,Stand still and separate the water layer into the bucket.Then transfer the toluene layer to the washing tank.Transfer the water layer to the reaction tank,Add 75 kg of toluene to the reaction tank.Stir,Rest,Separate the water layer,Combine the toluene layer into a water wash tank,Add 100kg of 25% salt water to the washing tank.Stir for 15 minutes,Let stand for 30 minutes,Divided into the water layer,Toluene solution of 4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate;The yield of amlodipine besylate was 91.1%, and the purity was 99.3%.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Liu Lijuan; Gao Huanhuan; Yu Yaoying; (13 pag.)CN108456160; (2018); A;,
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Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

Bromine (1.569 mL, 30.5 mmol) was added dropwise to an ice-cold solution of 5-nitro indoline (5 g, 30.5 mmol) in acetic acid (50 mL), and the mixture was stirred for 1 h. Acetic acid was concentrated under reduced pressure, and the resulting solid was triturated with water to afford the title compound (6 g, 80%) as a yellow solid, which was carried on to the next step without further purification. lU NMR (300 MHz, DMSO-i/6): delta 8.07 (d, J= 2.1 Hz, lH), 7.84 (d, J = 2.1 Hz, 1H), 7.3 (bs, 1H), 3.7 (t, J= 8.7 Hz, 2H), 3.17 (t, J= 8.4 Hz, 2H). ESI-MS m/z = 243 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHEUNG, Mui; TANGIRALA, Raghuram, S.; WO2014/81994; (2014); A1;,
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