Tag: M.W=100-200

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 324-03-8 as follows. Quality Control of 6-Fluoroindoline-2,3-dione

A solution of 6-fluoroindoline-2,3-dione (1 g, 6.06 mmol, SCRC) in anhydrous N,N-dimethylformamide (40 mL) was cooled to 00 C, whereupon NaH (60 % dispersion in mineral oil, 0.283 g, 7.09 mmol) was added in one portion and the reaction was stirred for 5minutes. lodomethane (0.443 mL, 7.09 mmol) was added and the reaction was stirred at 0 C for 30 minutes. The mixture was then poured into saturated aqueous NH4C1 and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (Mg504), filtered, and concentrated to give the crude product (1.2 g, 88 % purity), which was used without further purification.

According to the analysis of related databases, 324-03-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; HARDEE, David; BREWER, Jason; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; SCHRIMPF, Michael; SHEPPARD, George; (139 pag.)WO2018/188047; (2018); A1;,
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Synthetic Route of 59-48-3, 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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 5-Bromo-1,3-dihydro-indol-2-one. 5-Bromo-1,3-dihydro-indol-2-one can be prepared following the procedure described by Sun et al., J. Med. Chem., 41, 2588-2603 (1998).For example, to a stirred suspension of oxindole(1.30 g, 10 mmol) in dry acetonitrile(22.0 ML) at -10 C. was added portionwise recrystallized NBS (2.00 g, 11.0 mmol) and the resulting suspension was stirred at -10 to 0 C. for 3 hours.The suspension was allowed to warm to ambient temperature and the mixture was filtered to give a white solid which was recrystallized (EtOH) to provide the intermediate title compound (1.47, 43%) as a slightly pink solid; mp 212-214 C.

The synthetic route of Indolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bender, David Michael; Forman, Scott Louis; Jones, Winton Dennis; Smith, Daryl Lynn; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225127; (2003); A1;,
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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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Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
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Application of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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 21 3-[2,4-Dimethyl-5-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidene-methyl)-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 74 mg 4-methyl-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N of aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 60 mg (37%) of the title compound as a green solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.72 (s, br, 1H, NH-1), 7.50 (s, 1H, H-vinyl), 7.01 (t, J=7.82 Hz, 1H, H-6), 6.79 (d, J=7.82 Hz, H-5), 6.74 (d, J=7.82 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.56 (s, 3H, CH3), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.18 (s, 3H, CH3); MS m/z (relative intensity, %) 325 ([M+1]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methylindolin-2-one, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 141452-01-9

To a stirred solution of 4,6-dichloro-5-methylpyrimidine (101 mg, 0.62 mmol) in n- propanol (2.0 ml.) was added 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester {Bioorg. Med. Chem. Lett. 2008, 18, 5684 – 8) (100 mg, 0.56 mmol). The resulting yellow solution was heated at reflux (100 degrees Celsius). After 4 hours at reflux the reaction mixture was cooled to room temperature and was concentrated in vacuo. The reside was purified by flash chromatography, eluting with a gradient mixture of 10-40% ethyl acetate to heptane to give methyl 1-(6-chloro-5-methylpyrimidin-4-yl)indoline-5- carboxylate as a white solid (60 mg).

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; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem