Category: indolines-derivatives

These common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, 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. name: 1-Phenyloxindole

General procedure: General Procedure: Under nitrogen atmosphere, to a stirred solution of N-substituted-2-oxindole (10 mmol) in dry Et2O (40 mL) was added LiHMDS (1.0 M in THF solution, 12 mmol, 12 mL) dropwise at 0 C. The solution was allowed to warm to ambient temperature and stirred for 1 h. Then the solution was cooled to 0 C and TMSCl (13 mmol, 1.6 mL) was added dropwise. The solution was allowed to warm to ambient temperature and stirred for another 3 h. The solvent was removed under reduced pressure, and dry MeCN (40 mL) was charged to the flask. The solution was cooled to 0 C again and Selectfluor (12 mmol, 4.3 g) was added to the solution in small portions. The resulting suspension was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by the addition of water (20 mL) and EtOAc (20 mL). The reaction mixture was extracted with EtOAc (20 mL × 2). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure Purification of the crude product was performed by flash column chromatography (Hexane/EtOAc) to afford 3-fluorooxindole.

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

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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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 7147-90-2 as follows. Recommanded Product: 5-Chloroisoindoline-1,3-dione

c 4-Chloro-N-(3,3,3-trifluoropropyl)phthalamic acid 3.6 g of 1,1,1-trifluoro-3-iodopropane are added dropwise to a mixture of 7.5 g of 4-chlorophthalimide and 4.6 g of potassium carbonate in 40 cm3 of dimethylformamide at a temperature in the region of 110 C. with stirring. After stirring for 11 hours at a temperature in the region of 120 C., the reaction mixture is cooled to a temperature in the region of 20 C. and then poured into 200 cm3 of water. The mixture is acidified with dilute aqueous hydrochloric acid solution to a pH of about 3, and is then extracted 3 times with 100 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate and then concentrated to dryness. 5.0 g of 4-chloro-N-(3,3,3-trifluoropropyl)phthalamic acid are thus obtained, Rf=0.12 (thin layer chromatography on silica gel, eluent: ethyl acetate).

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Deuschland GmbH; Aventis Pharma S.A.; US2004/48916; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-1,3-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 89-40-7, Recommanded Product: 5-Nitroisoindoline-1,3-dione

5: A mixture of 4-nitro-phthalimide 4 (8.02 g, 0.042 mol) and hydrochloric acid (26 %, 290 mL) was heated at 50 C for 2 h. Then the resulted yellow solution was cooled to room temperature. The precipitate was collected by filtration and recrystallized from ethanol dried in vacuum affording a light yellow solid 5 (7.44 g, 89% yield). 1H NMR (DMSO-d6): delta (ppm) 10.77 (s, 1H, CONHCO), 7.45 (d, J1 = 8.0, 1H, Ar-H), 6.92 (d, J2 = 2.0 Hz, 1H, Ar-H), 6.86 (dd, J1= 8.0, J2 = 2.0 Hz, 1H, Ar-H). 5.06 (s, 2H, NH2). 13CNMR (DMSO-d6): delta (ppm) 169.44, 169.26, 150.64, 135.22, 124.73, 121.51, 120.11, 109.64.

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, 5-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Song, Xiaoyu; Zhao, Jing; Zhang, Wandong; Chen, Long; Chinese Chemical Letters; (2018); p. 331 – 335;,
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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. 84575-27-9, name is 7-Methoxyindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H7NO3

General procedure: To a stirred solution of ethyl 2-(triphenylphosphoranylidene)acetate (3.83 g, 11.0 mmol) in CH2Cl2 (30.0 mL) was added isatin (1.47 g, 10.0 mmol) at 0 C. After stirring for 8 h at 0 C, the mixture was concentrated by rotary evaporation. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=3:1-10:1) to afford the compound 1a as a red solid (1.78 g, 82 %).

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 84575-27-9.

Reference:
Article; Zhao, Jia; Guan, Shuicheng; Zhou, Xiaojian; Han, Wenyong; Cui, Baodong; Chen, Yongzheng; Tetrahedron; vol. 72; 22; (2016); p. 3098 – 3104;,
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Related Products of 2058-72-2,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.

General procedure: A mixture of isatin derivatives 3 (1 mmol), proline 4 (1 mmol, 0.115 g) and chiral cinamoyl oxazolidinone 1 (1 mmol, 0.293 g) was dissolved in EtOH (80%) (5 mL) and stirred at room temperature for about 5 h. After completion of the reaction (TLC), the solvent was evaporated under reduced pressure, the products (5a-i) were obtained in quantitative yields; and for future purification they were washed with cold EtOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Taghizadeh, Mohammad Javad; Arvinnezhad, Hamid; Samadi, Saadi; Jadidi, Khosrow; Javidan, Abdollah; Notash, Behrouz; Tetrahedron Letters; vol. 53; 38; (2012); p. 5148 – 5150;,
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Electric Literature of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: First, 0.01g of the CoFe2O4(at)SiO2(at)SO3H was dispersed for 30min and after that an amount of 1mmol from isatin, malononitrile and dimedone with ethanol/water (ratio 1:1) were mixed, and the final mixture was placed in 80C at the reflux condition. After completing the reaction by passing a certain time, the con -taining solution was separated by centrifuging and the crude product extracted and washed with ethyl acetate, and then Na 2 SO 4 was added to dehydrating the product. After that, the solvent was removed by using a rotary evaporator and finally the product recrystallized in hot ethanol to gain the pure product. Moreo -ver, the catalyst was washed and applied for several times to examine reusability. Structural assignments of the products are based on their 1 HNMR, 13 CNMR and IR spectra.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zamani-Ranjbar-Garmroodi, Bardia; Nasseri, Mohammad A.; Allahresani, Ali; Hemmat, Kaveh; Research on Chemical Intermediates; vol. 45; 11; (2019); p. 5665 – 5680;,
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Electric Literature of 13861-75-1, 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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,2-dihydro-3-spiro-1′-cyclopropyl-1H-indole-2-one (2.5 g crude) in THF (50 mL) was added LiAlH4 (2 g, 52 mmol) portionwise. After heating the mixture to reflux, it was poured into crushed ice, basified with aqueous ammonia to pH 8 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the crude 1,2-dihydro-3-spiro-1′-cyclopropyl-1H-indole as a yellow solid (about 2 g), which was used directly in the next step.

The synthetic route of Spiro[cyclopropane-1,3′-indolin]-2′-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 7-Methylindoline-2,3-dione

General procedure: Mg(ClO4)2 (10 mol %) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50%, v/v, 5 mL), and the resulting mixture was stirred at 50C for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 × 30 mL) and cold aqueous ethanol (2 × 1 mL) to afford pure product 4.

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
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Synthetic Route 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.

Weigh5-nitroindole-dione 5.00g (26.02mmol) into a 250mL round bottom flask was added150mL of cyclohexane under stirring conditions, neopentyl glycol was slowlyadded 2.98g (28.63mmol), of methylbenzenesulfonate 0.896g (5.20mmol), thenheated at reflux at 100 6h.Starting material disappeared on TLC, cooled to room temperature, suctionfiltered, washed with a saturated aqueous sodium hydrogen carbonate builders,and dried under vacuum oven to give 5-nitro-3,3-shrink glutaraldehyde newindolinone 6.63g, yield 91.6%.

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:
Patent; Tianjin University of Science&Technology; Yu, peng; Liu, fengxi; sun, HUA; Teng, yuou; Guo, qiannan; Han, kailin; Li, Huan Huan; Yang, yao; song, BINBIN; (19 pag.)CN103554008; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 6872-06-6, name is 2-Methylindoline, 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 6872-06-6, Recommanded Product: 2-Methylindoline

General procedure: The mixture of xylene (1.0 mL), substrate (0.3 mmol), and rGO (100 w%) was stirred at 100 C for 12 h under O2 atmosphere. After the reaction, the mixture was diluted with AcOEt and water. The organic phase was concentrated under reduced pressure, and purified by column chromatography with silica gel.

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-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; 1; (2016); p. 21 – 23;,
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