Tag: M.W=100-200

Related Products of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL¡Á2) to afford the pure products as solid powder in good to excellent yields without further purification.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
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Application of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

6-chloroindolin-2-one (8.35 g, 50 mmol) and 3-chloro-2-fluorobenzaldehyde (8.295 g, 52.5 mmol) were stirred at reflux for 6 hours in the presence of piperidine (1 ml). Then filter the reaction suspension, The collected solid was washed with methanol and dried to give (E)-6-chloro-3-(3-chloro-2-fluorobenzylidene)indol-2-one product (14.63 g, 47.5) as a yellow solid. Mmol), yield 95%.

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; Xiao Fei; Ma Jie; Ren Hongjun; Wang Wei; Xu Hongtao; Wang Meng; Zou Lihui; Ding Fei; Su Fei; (37 pag.)CN107698598; (2018); A;,
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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 1504-06-9 as follows. SDS of cas: 1504-06-9

To a Schlenk reaction flask with a volume of 20 mL, 0.2 mmol of 3-methyl-2-indanone, 0.4 mmol of morpholine, 0.04 mmol of I2, 0.4 mmol of H 2 O 2 and ethanol (2 mL) were added.The reaction flask was stirred at room temperature under an air atmosphere, and the progress of the reaction was monitored by TLC or GC until the reaction of the starting material was complete (8 hours).The reaction mixture after completion of the reaction was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / petroleum ether).

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Gao Lehan; Wei Wenting; Bao Wenhui; Xu Xudong; Wang Yining; (10 pag.)CN108440378; (2018); 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. 21857-45-4, name is 5-Methoxyindoline, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO

A solution of the product Step A (0.32 g; 2.14 mmol) in 48% HBr/ AcOH 1 :1 (10 ml) was refluxed overnight, then evaporated to dryness under reduced pressure. The residue was dissolved in EtOH (10 ml) and the solvent was removed under reduced pressure. This process was repeated three times and the residue was suspended in acetonitrile. The greyish solid formed was filtered off, washed with fresh CH3CN and dried to give a hydrobromide salt of the title compound (0.28 g; 60%). . 1 H-NMR (D2O ) 3.18 (tr, 2H, J = 7.8 Hz); 3.78 (tr, 2H, J = 7.8 Hz); 4.66 (HDO); 6.78 (d, 1 H, J = 8.6 Hz); 6.87 (s, 1 H); 7.23 (d, 1 H, J = 8.6 Hz).

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; AKAAL PHARMA PTY LTD; GILL, Gurmit, S.; GROBELNY, Damian, W.; WO2010/42998; (2010); A1;,
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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 20870-79-5 as follows. name: 5-Nitroindolin-2-one

A. A suspension of 5-nitroindolin-2-one (2.0 g, 11.13 mmol), and 10% palladium on carbon (500 mg) in methanol (100 mL) was hydrogenated for 2 hours under 45 psi. The reaction mixture was filtered through celite and the resulting cake was washed with methanol. The filtrate was concentrated to afford 5-aminoindolin-2-one as a tan-colored solid (1.6 g).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Aktiengesellschaft; US2005/90541; (2005); A1;,
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Related Products of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Activation of 2-(2-hydroxyethyl)isoindoline-1,3-dione to Form VA To the mixture of commercially available 2-(2-hydroxyethyl) isoindoline-1,3-dione (8.8 g. 1.00 equiv) and triethylamine (5.8 g, 1.25 equiv) in methylene chloride (69 mL) is added benzenesulfonyl chloride (9.3 g, 1.05 equiv) dropwise at under about 25 C. The mixture is stirred at room temperature until the reaction is complete as determined by HPLC. The reaction mixture is washed with an aqueous solution of sodium bicarbonate. The organic solution is concentrated under reduced pressure and the product is precipitated by adding hexanes (83 mL) to the residue. VA is isolated by filtration (15.1 g, 99% yield). 1H NMR (400 MHz, DMSO-d6): delta 7.77-7.82 (m, 4H), 7.71 (d, J=8.0, 2H), 7.52 (t, J=8.0, 1H), 7.41 (t, J=8.0, 2H), 4.29 (t, J=4.0, 2H), 3.81 (t, J=4.0, 2H).

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

Reference:
Patent; Gilead Sciences, Inc.; Chiu, Anna; Feng, Yanshu; Gao, Hanrong; Kerschen, James A.; Reichwein, John; Sarma, Keshab; Thompson, Andrew S.; Zhao, Xinjun; US2015/225384; (2015); A1;,
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Synthetic Route of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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.

Step 11b, Example 26b: (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 42 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 22 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.2 ml of pyridine, and then 33 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water, then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (+)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (18 mg) in the form of a pulverulent solid (yield=31%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=+19 C.=0.950 mg/0.5 ml in DMSO

Statistics shows that 4-Chloroindoline is playing an increasingly important role. we look forward to future research findings about 41910-64-9.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
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Reference of 52537-00-5,Some common heterocyclic compound, 52537-00-5, name is 6-Chloro-2,3-dihydro-1H-indole, molecular formula is C8H8ClN, 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 208b Preparation of rac-6,6′-Dichloro-3′-(3-chloro-benzyl)-2,3,1′,3′-tetrahydro-[1,3′]biindolyl-2′-one The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.27 mmol) (from example 1c supra), 6-chloro-2,3-dihydro-1H-indole (62 mg, 0.45 mmol) and K2CO3 (110 mg, 0.80 mmol) in DMF (1 mL) was stirred at room temperature overnight. Then water (10 mL) was added and the desired product was precipitated out. The crude product was purified by prep-HPLC to give 55 mg rac-6,6′-Dichloro-3′-(3-chloro-benzyl)-2,3,1′,3′-tetrahydro-[1,3′]biindolyl-2′-one. MS: [M+H]+=443

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-2,3-dihydro-1H-indole, its application will become more common.

Reference:
Patent; Chen, Li; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2008/81810; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 58083-59-3, name is 6-Chloroisoindolin-1-one, 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 58083-59-3, Safety of 6-Chloroisoindolin-1-one

A. A solution of 151 g of triethyloxonium tetrafluoroborate in 3200 ml of methylene chloride was stirred under argon at room temperature for 3.5 hours after the addition of 106.6 g of 6-chloro-2,3-dihydro-1H-isoindol-1-one. The mixture was then treated within 40 minutes with 1.28 l of saturated sodium hydrogen carbonate solution, the organic phase was separated and washed with 1.28 l of water. After drying over sodium sulphate the organic phase was filtered and evaporated. The residue was taken up in 1.3 l of diethyl ether, whereupon it was stirred at room temperature for about 30 minutes. After removing insoluble material by filtration the filtrate was evaporated. There was obtained 110.5 g of 1-ethoxy-6-chloro-3H-isoindole with a m.p. of 64¡ã-66¡ã.

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; Hoffmann-La Roche, Inc.; US5143912; (1992); 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 17564-64-6

(Bis(trimethylsilyl)amino)lithium (2.4 mL of a 1 M solution in THF, 2.4 mmol) was added dropwise to a solution of benzyl 3,3-dimethyl-4-oxo-piperidine-1-carboxylate (500 mg, 2 mmol) in THF (7 mL) at -78 C under N2. After 90 minutes, a solution of 2- (chloromethyl)isoindoline-1,3-dione (560 mg, 3 mmol) in THF (2 mL) was added. The reaction mixture was stirred for 1 hour then quenched by the addition of saturated aqueous NH4Cl solution (~2 mL). The reaction mixture was diluted with EtOAc, washed with a saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, PE/EtOAc gradient elution) and then by reverse phase chromatography (C18, MeCN / water- 0.1% ammonium hydroxide as eluent) to give benzyl 5-[(1,3-dioxoisoindolin-2-yl)methyl]-3,3-dimethyl-4-oxo-piperidine-1- carboxylate as a colourless oil (180 mg, 21%); MS m/z: 421 (M+H)+.

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; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
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