Author: tianli

Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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. 2058-72-2

General procedure: To a stirring mixture of catalyst 1a (0.005 mmol) and cyclohexanone/acetone (5 mmol) in water (500 muL), additive DNP (0.920 mg, 0.005 mmol) was added at 25 C and the mixture was allowed to stir for 5 min followed by addition of isatin derivative (0.5 mmol). The mixture was stirred for 20-96 h and the progress of the reaction was monitored at regular intervals by TLC. On the completion of reaction, saturated solution of NH4Cl (5 mL) was added to it and resulting mixture was extracted with ethyl acetate (3¡Á15 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude aldol product. The column chromatography on silica gel (60-120 mesh) using hexane/ethyl acetate as an eluent gave the corresponding aldol adducts as a syn/anti mixture. The enantiomeric excess of aldol addition products was determined by chiral HPLC. The diastereoselectivity of product was determined by HPLC of crude reaction mixture. Racemic standards were prepared using (¡À) 3-methyl-1-morpholinobutan-2-amine catalyst synthesized form (¡À) valine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-72-2, its application will become more common.

Reference:
Article; Kumar, Akshay; Chimni, Swapandeep Singh; Tetrahedron; vol. 69; 25; (2013); p. 5197 – 5204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6326-79-0 name is 6-Bromoisatin, 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. 6326-79-0

Step 1: Synthesis of Intermediate 1-5.1To RiO (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 mL, 241 mmol) and K2C03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, is dried over MgSO4 and concentrated. Yield 56%, m/z 240/242[M+H]+, rt 0.48 mi LC-MS Method X001 004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6326-79-0 name is 6-Bromoisatin, 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. 6326-79-0

To R7 (25.0 g, I I I mmol) in acetonitrile (750 mL) is added Mel (15 mL, 24ltnmol) and KzC03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, dried over MgS04 and concentrated. Yield 56%, mlz 240/242 [M+H]+,rt 0.48 min, LC-MS Method XOOl_ 004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

104618-32-8, A common compound: 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of commercially available 3-bromophenyl hydrazine (2.74 g, 12.2 mmol) in ethanol (100 mL) was added ketone derivative (3 g, 12.2 mmol) in ethanol (50 mL). The reaction mixture was stirred for 5 h at room temperature. The solvent was removed to give the title compound as a solid (5 g, quantitative). The product was used in the next step without any purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5, 2913-97-5

1, 4 g of N- (2-acetaldehyde) phthalimide,3 g of N, N’-dihydroxy-2,3-dimethyl-2,3-butanediamine was dissolved in 70 mL of 60percent ethanol aqueous solution,0.1 ml formic acid was added dropwise and the reaction was stirred at 25 ¡ã C for 24 hours.Suction filtered and washed to give a white solid product A 4.2 g,Yield 65percent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-(2-Oxoethyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Normal University; Shi Zhiqiang; Li Jiaofu; Wang Yongxia; (8 pag.)CN104557714; (2017); B;,
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 2058-72-2 as follows. 2058-72-2

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below., 1074-82-4

50 mL of DMF, 0.025 mol of the potassium salt of phthalimide, 0.10 mol of 1,4-dibromobutane and 0.5 g of TBAB, reaction at 70 C. for 2.0 h; cooling to room temperature, pouring into ice water, extraction with ethyl acetate, After washing with water, drying and desolvation, the mixture was allowed to stand overnight to precipitate 5.82 g of N-(4-bromobutyl)phthalimide as a white solid, mp 78-81C, yield 82.5%.

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:
Patent; Hunan University; Hu Aixi; Yang Zihui; Li Jingwen; (9 pag.)CN107540647; (2018); 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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 2518-24-3

60.0 g (370.0 mmol) of 3-aminophthalimide (18), 900 cm3 of acetonitrile, 93.6 g (925.0 mmol) triethylamine are measured into a 2000 cm3 round-bottomed flask, then the suspension obtained in this way is cooled to 0 C. While stirring a solution made of 60.23 g (555.0 mmol) of ethyl chloroformate (19, R = Et) with 120 cm3 of acetonitrile is added over the course of 60 minutes, whilst maintaining the temperature between 0-5 C the stirring is continued at this temperature for 1 to 2 hours. The reaction mixture is left to warm up to room temperature and the stirring is continued for 1 hour. Using a vacuum the reaction mixture is concentrated to 200 cm3, then a solution of 3.0 cm3 cc. hydrochloric acid made with 900 cm3 of distilled water is added to it. The suspension is again cooled to 0 to 5 C and then stirred at this temperature for 30 to 60 minutes. The crystalline product is filtered, washed with 2x 120 cm3 of solvent mixture (acetonitrile/water = 1/4), then dried in a vacuum at 50 C until constant weight is achieved. In this way 78.28 g (90.3%) of the product according to the title is obtained, which is taken to the next reaction without purification. Mp.: 158-159 C IR (KBr): 3457, 3355, 1783, 1758, 1640, 1169 cm 1. 1H NMR (DMSO-d6, 400 MHz): delta = 7.52 (m, 1H), 7.06 (m, 1H), 7.03 (m, 1H), 6.72 (b, 2H), 4.33 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H) ppm. HPLC: Waters Acquity UPLC BEH C18; 2.1 x50 mm; 1.7 mum; 0.5 mL/min; 225 nm; 10/90 CH3CN/0.1 % HClO4 (aq); 1.90 min (99.70%).

The synthetic route of 2518-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EGIS GYOGYSZERGYAR ZRT.; VOLK, Balazs; KATAINE FADGYAS, Katalin; LUKACS, Gyula; TOTHNE LAURITZ, Maria; DANCSO, Andras; KIRALY, Imre; PALOTAI, Laszlo; KORMANY, Robert; (25 pag.)WO2017/134476; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 2058-74-4, name is 1-Methylisatin, I believe this compound will play a more active role in future production and life. 2058-74-4

To the solution of Isatin 1a (1 mmol) in water (20 ml)at 60 C was added o-phenylenediamine 2 (1 mmol). The resulting mixture was stirred and beta-cyclodextrin(15 mol%) was added to the solution. The reaction progress was monitored using TLC by mixture of Hexane – EtOAc (6/4). The completion of the reactionas indicated by TLC in UV-chamber and vapour iodine chamber. The reaction mixture was cooled to room temperature and mixture was extracted by ethyl acetate(2 30mL) and dried over anhydrous sodium sulfate.Ethyl acetate removed in vacuum and crude product obtained. To recycle beta-cyclodextrin, acetone was added in the aqueous media, beta-cyclodextrin recovered. Pure product (6H-Indolo[2,3-b]quinoxaline3a) was obtained by silica gel column chromatography(Hexane/EtOAc) = (7/3 – 6/4) as solid.

The chemical industry reduces the impact on the environment during synthesis 2058-74-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shivhare, Km Neha; Siddiqui; Supramolecular Chemistry; vol. 31; 1; (2019); p. 52 – 61;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem