Month: March 2021

These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Formula: C9H7NO3

Compound 7 (1.00 g, 0.006 mol) was dissolved in dry MeOH (40 ml) and cooled down to -10C. Thionyl chloride (0.91 ml, 0.012 mol) was added dropwise. The reaction mixture was stirred at reflux temperature for 2 hours. TLC monitoring of the reaction was performed on silica gel plates using ACN:MeOH:H2O (10:1:1) as eluent. The solution was poured onto crushed ice (100 ml) and extracted with EtOAC (3 x 100 ml). The combined organic phase was dried over MgSO4 and evaporated to give a greyish solid (755 mg).

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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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 6872-06-6 as follows. Application In Synthesis of 2-Methylindoline

(1) 1.19 g of 2-methylindoline and 2.57 g of 2-bromo-4-methylpyridine were added to a 50 mL round bottom flask in a ratio of the amount of the substance: 1:1.5; (2) Stir directly in the air and mix evenly at room temperature.Then heated to 100 C, after 26 min the system solidified, stopped the reaction, cooled to room temperature; (3) Add 50 mL of saturated NaHCO3 solution to the system to dissolve the solid.Further, 50 mL of ethyl acetate solution was added, shaken, and liquid-separated, and the aqueous phase was extracted three times with ethyl acetate, 30 mL each time, and the organic phase was combined and concentrated by a rotary evaporator; (4) The concentrated solution was dissolved in 15 mL of ethanol, refluxed at 80 C for 10 min, cooled, and a pale yellow solid was precipitated, filtered, rinsed with water and dried under vacuum to give the desired product.The purity was 97% (NMR analysis) and the yield was 75%.

According to the analysis of related databases, 6872-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Northwest University; Jiao Linyu; Zhang Ze; Yin Xiaomei; Hong Qian; Ning Zihui; Ma Xiaoxun; Li Zhuo; Sun Ming; (11 pag.)CN109265439; (2019); A;,
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Indoline | C8H9N – PubChem

Related Products of 35197-64-9, These common heterocyclic compound, 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, 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.

To a solution of 2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid (2) (2.51g; 8.04mmol), thionyl chloride (20mL; 0.27mol) was added and the resulting solution was refluxed for three hours. The excess unreacted thionyl chloride was removed under reduced pressure and the resulting acid chloride was used in the next step as such. To the ice-cooled and stirred solution of the obtained above acid chloride in dry THF (30mL), the N-benzylamine derivative (24.13mmol) was added dropwise and stirring continued for three hours and left overnight. The reaction mixture was poured into ice. The organic layer was washed with dil. HCl and evaporated under vacuum. The aqueous layer was extracted with DCM. The combined organic layers were dried (NaSO4) and concentrated in vacuo. The crude product was finally purified by column chromatography (DCM/acetone 9:1 v/v).

Statistics shows that 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid is playing an increasingly important role. we look forward to future research findings about 35197-64-9.

Reference:
Article; Kowalczyk, Paula; Sa?at, Kinga; Hoefner, Georg C.; Mucha, Marta; Rapacz, Anna; Podkowa, Adrian; Filipek, Barbara; Wanner, Klaus T.; Kulig, Katarzyna; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 256 – 273;,
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Indoline | C8H9N – PubChem

Application 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.

7-Fluoro-N-methylisatin (IVa). To a solution of IIIa (380 mg, 2.30 mmol) in dry acetone (60 mL) was added Na2CO3 (anh.) (3.5 g) and dimethylsulfate (0.4 mL) under Ar and the reaction mixture was heated at 60 C. for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C.). The solid residue was submitted to flash chromatography with CH2Cl2 to afford IVa (288 mg, 1.61 mmol, 70%).

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; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE PIERRE ET MARIE CURIE; UNIVERSITE DE RENNES I; UNIVERSITY OF LLEIDA; UNIVERSITE D’ATHENES; US2010/331327; (2010); A1;,
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 61-70-1 as follows. COA of Formula: C9H9NO

N-methyl-2-indolone (1a, 0.3 mmol), t-butyl nitrite (t-BuONO, 2a, 1.2 mmol) and water (2 mL) were added to 10 mL of Schlenk bottles, The reaction mixture was then stirred at 25 C, the reaction was monitored by TLC or GC, and the reaction was complete with the reaction of N-methyl-2-indolone, The organic phase was extracted with ethyl acetate and the organic phase was combined. The organic phase was dried over anhydrous sodium sulfate, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was dried over anhydrous sodium sulfate, The residue was isolated by column chromatography (n-hexane / ethyl acetate) to give the desired product N-methyl-isato-3-oxime I-2 in 75% yield.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Wu Yi; Wei Wenting; Zhu Wenming; Huang Yiling; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107162951; (2017); A;,
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;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84378-94-9, name is 4-Chloro-5-fluoroindoline-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 84378-94-9, Computed Properties of C8H3ClFNO2

Anthranilic acid was added 0. Olmol equipped with a reflux condenser, a magnetic sub, thermometer, three-necked flask below, by adding toluene 15mL, dried S0C12 3mL, reflux 1. 0h, to stop the reaction, the solvent was removed by rotary evaporation under reduced pressure and excess the S0C12. Beyond flask square. OlmoL 4-chloro-5-fluoro-isatin and 15mL of dichloromethane, the reaction continued at reflux for 1. 0h, cooled to room temperature and filtered to give a yellow solid, washed with methanol lotions, dichloro recrystallization from toluene or methane. In this method for the synthesis of the following target product.

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, 4-Chloro-5-fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Northwest University; Huo, Baolong; Wang, Cuiling; (52 pag.)CN105330666; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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.

General procedure: The mixture of the Fe(III)(at)g-C3N4 nanocomposite (70 mg, 0.35 mmol based on Fe(III)) in aqueous media (3 ml) was dispersed for 30 min. Isatin (1 mmol) and indole (2.0 mmol) were added to the mixture and stirred in reflux conditions for an appropriate time. After the reaction was completed, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4 followed by evaporation of the solvent. The pure products were achieved by recrystallization in hot ethanol and identified by IR, 1H & 13C NMR spectral data. The nanocomposite was washed with EtOH, dried, and reused for the next run.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6741 – 6751;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 239463-85-5,Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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 9: Preparation of SilodosinProcedure 1: To a solution of Tartrate salt of 3-(5-((R)-2-aminopropyl)-7- cyanoindolin-l-yl) propyl benzoate (I) (50, 0.097 mol) in ethyl acetate (500 ml) was added water (500 ml) followed by addition of aqueous solution of Potassium carbonate (Potassium carbonate (130 g) dissolved in water (200 ml)). The mixture was stirred for lh at room temperature and the layers were separated. The organic layer was washed with water (500 ml) and concentrated under reduced pressure. The obtained crude was dissolved in Isopropyl alcohol (750 ml), Sodium carbonate (11.3 g, 0.107 mol) and 2- [2-(2,2,2-trifluoroethoxy)phenoxy]ethyl methane sulfonate of Formula XIII (36.7 g, 1.16 mol) were added. The mixture was stirred at 80C for 40-50 h. After completion of the reaction, the mixture was cooled and water (500 ml) was added. The organic layer was extracted with ethyl acetate twice (2 x 500 ml). The combined organic layers were evaporated to obtain the product and the product obtained was purified by column chromatography using dichloromethane and methanol in different ratios as a mobile phase. The appropriate fractions were combined together and distilled under reduced pressure to give 38 gm of 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)- phenoxy]ethyl}amino)propyl)-2,3-dihy dro-lH-indol-l-yl) -propyl benzoate of Formula XIV (HPLC purity: 99.5%).The conversion of Formula XIV to Silodisn was followed by procedures disclosed in any of the prior art including United States patent application 20070197627 and United States patent 5,387,603.

The synthetic route of 239463-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PANACEA BIOTEC LTD; JAIN, Rajesh; RAO, Jagadeeshwar R; RAO, Siripragada Mahender; WO2012/131710; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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. category: indolines-derivatives

Diethylaminotrifluorosulfur (1.5 mL, 11.06 mmol) was added to a solution of 4-bromo-1H-indole-2,3-dione (1.0 g, 4.4 mmol) in dichloromethane (44 mL) at 0¡ãC. The mixture was stirred at room temperature for 54 hours and then quenched with methanol-water. The organic layer and the aqueous layer were separated, and the aqueous layer was then extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-bromo-3,3-difluoro-1,3-dihydro-indol-2-one as a yellow solid (559 mg, 51percent). MS (ESI) m/z = 246 (M-H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20780-72-7, its application will become more common.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2433940; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem