Category: indolines-derivatives

Synthetic Route of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.

3 – (3 -chlorophenyl) propyne acid 4 – nitrophenyl-unitz (90.3 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 44 mg and gave rise 88% to unit_.

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

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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Related Products of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatin derivatives 1 (1 mmol), 1-aryl-2-thiocyanatoethanone 2 (1 mmol) and Et3N (1mmol) in EtOAc (3 mL) was stirred at room temperature for 8 h. Then hydrazonoyl chloride 3 (1mmol) was added to the above mixture and the reaction was stirred at reflux temperature for 10min. After completion of the reaction, the reaction mixture was filtered, EtOAc was evaporated andthe residue was purified by recrystallization from ethanol to afford the pure product 4 in high yield.The two disterioisomers of products 4a-c were separated by washing the precipitate with n-Hexane/EtOAc (10/1)

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Synlett; vol. 27; 12; (2016); p. 1828 – 1831;,
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Related Products of 102359-00-2, 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 102359-00-2 as follows.

EXAMPLE 43 5-Carboxyoxindol (0.93 g) and 0.8 ml of trimethylamine were suspended in 10 ml of tetrahydrofuran (THF), and a solution of 1.0 g of diethylchlorophosphate in 10 ml of THF was added dropwise thereto at room temperature with stirring. The mixture was stirred for 3 hours at room temperature. To the mixture was added dropwise a solution of 1.1 g of benzylpiperazine in 10 ml of THF and was further stirred for 10 hours at room temperature. After completion of reaction, crystals which precipitated were filtered off and the filtrate was concentrated. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and the mixture was extracted with chloroform. Organic layer was washed with water and a saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off. Recrystallization of the residue from isopropyl alcohol gave 1.01 g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. m.p.: 151-153 C.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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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. 261732-38-1, name is tert-Butyl 5-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 261732-38-1

A solution of 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (4. 0 g, 13.5 mmol), tributylamine and bis-triphenylphosphinopalladium(II) chloride (0.65 g, 0.926 mmol) in methanol was sealed in a Parr pressure apparatus and pressurized with 600 psi of carbon monoxide. The solution was heated at 100 C for one week. The vessel was cooled to room temperature and the gas vented. The solution was filtered, and the solvent was evaporated in vacuo. The residue was purified by flash chromatography, on silica gel eluted with 10-40% ethyl acetate in hexane to give the product mixed with tributylamine, 2.5 g (67%). The product was used without further purification in the subsequent step.

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; JANSSEN PHARMACEUTICA N.V.; WO2004/69792; (2004); A2;,
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Related Products of 5428-09-1, These common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-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.

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

Statistics shows that 2-Allylisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5428-09-1.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
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Application of 2307-00-8, These common heterocyclic compound, 2307-00-8, name is 5-Amino-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.

4-N-Ethylamino-N-methylphthalimide (5) A mixture of 10 g (0.057 mol) of 4-amino-N-methylphthalimide (4) [Flitsch, Chem. Ber. 94:2494(1961)], 17.5 g (0.11 mol) of diethyl sulfate, and 100 ml of 2,2,2-trifluoroethanol was refluxed for one day. The reaction mixture was cooled, concentrated under reduced pressure, and the residue partitioned between 250 ml of ethyl acetate and 100 ml of saturated sodium bicarbonate solution containing 10 ml of triethylamine. The ethyl acetate phase was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was recrystallized twice from acetone-hexane and then from aqueous methanol to give 3.4 g (29% yield) of the phthalimide (5) as fine yellow crystals, m.p. 157 C. Analysis: Calculated for C11 H12 N2 O2: C, 64.69; H, 5.92; N, 13.71; Found: C, 64.00; H, 5.71; N, 13.37. NMR Spectrum (C5 D5 N): delta 0.5 (t, J=7 Hz, 3H), 2.1 (s, 3H)

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miles Laboratories, Inc.; US4363759; (1982); A;,
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Related Products of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

5.4. Example 4; To a solution of powdered LiOH (17.25 g, 1.5 eq) in anhydrous methanol (600 ml) was added cyanoacetamide (63 g, 1.5 eq) under nitrogen atmosphere. The resulting mixture was stirred for 20 min at room temperature. To this was added a solution of phthalimidoacetone (101.5 g, 0.5 mol) in 700 ml of THF (anhydrous) over a period of 30 min. Resulting reaction mixture was stirred for 2 h at room temperature and then heated at 55 C. for 1 h. To this was added sodium methoxide solution (25% solution, 172 ml, 1.5 eq) at 55 C. over a period of 40 min. After 3 h HPLC/MS indicated starting material and intermediates were converted to 2-amino-4-methyl-1H-pyrrole-3-carboxamide. To this reaction mixture was added ethyl formate (200.8 ml, 5 eq) over a period of 20 min followed by sodium methoxide (25% solution, 324 g, 3 eq). The resulting reaction mixture was heated for 7 h at 55 C. at which time HPLC/MS indicated that the intermediate pyrrole compound was converted to the final product. The reaction mixture was diluted with 1.5 L water, heated at 60 C. for 1 h, and then concentrated to small volume (11.5 L). Solution assay indicated that final product was formed in 75% solution yield. This solution was acidified to pH 7.5 with 6 N aq. HCl, cooled to about 5 C., and held at this temperature for 30 min. The solid was filtered, washed with water, dried at 50 C. under vacuum overnight to give the final product as a light brown solid (45.8 g, 61% yield, purity: 99.0% by HPLC area).

The chemical industry reduces the impact on the environment during synthesis 2-(2-Oxopropyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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 334952-09-9, SDS of cas: 334952-09-9

Example 81 3-[4-(2-Diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid (80 mg, 0.45 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide to give 210 mg (92%) of the title compound as a yellow orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.6 (s, 1H, NH), 7.76 (d, J=8.0 Hz, 1H), 7.66 (s, 1H, H-vinyl), 7.57 (dd, J=1.5 & 8.0 Hz, 1H), 7.40-7.42 (m, 2H), 3.28 (m, 2H, CH2), 2.88 (m, H-piperidine), 2.54 (m, 6H, 3*CH2), 2.44 (s, 3H, CH3), 2.40 (s, 3H, CH3), 1.56 (m, H-piperidine), 0.97 (t, J=6.98 Hz, 6H, N(CH2CH3)2). MS m/z 424 [M+].

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:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
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Reference of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of substituted isatins (1 mmol),cyclic 1,3-diketone (1 mmol), malononitrile (1 mmol)and nano Ag/kaolin (0.085 g, 7 mol%) in EtOH (10mL) was stirred at reflux temperature. Uponcompletion instead of compilation, monitored by TLC(n-hexane/ethyl acetate: 2/1), the reaction mixture wasallowed to cool to room temperature. The catalyst wasseparated by filtration of this solution. The solution wasconcentrated under vacuum to afford the product,which was purified by recrystallization in the ethanol.All the products were identified by comparing of meltingpoint and 1H NMR spectra with those of authenticsamples reported in the literature.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sadeghi, Bahareh; Lasemi, Zahra; Azimi, Razieh; Oriental Journal of Chemistry; vol. 31; 2; (2015); p. 1175 – 1179;,
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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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6BrNO2

General procedure: General procedure forthe preparation of oxazolo[5,4-b]quinoline- fused spirooxindoles 4a-t: A reaction of isatin(1 mmol),beta-diketone (1 mmol) and5-amino-3-methylisoxazole (1 mmol) were mixed and irradiated in a closed vesselin the absence of any solvent in a Synthos 3000 microwave reactor at 700 W, 14 bar,and 110 C for 10 min. The reaction was monitored by TLC. Then, thereaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

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:
Article; Yuvaraj, Panneerselvam; Manivannan, Karthikeyan; Reddy, Boreddy S.R.; Tetrahedron Letters; vol. 56; 1; (2015); p. 78 – 81;,
Indoline – Wikipedia,
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