Author: Jessica.F

Electric Literature of 50727-04-3, 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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-methoxyphthalic anhydride (27.8 g, 0.16 mol) and formamide (175 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. The solid material was filtered off, washed sequentially with water (100 ml), 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford A- methoxyphthalimide (21.3 g, 77%) as a pale yellow solid. 1H NMR (DMSOd6) 11.15 (1 H, br s), 7.74 (1 H, d), 7.33-7.28 (2H, m), 3.92 (3H, s). A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSO-CJ6) 7.13 (1H, d), 6.84 (1H, d), 6.74 (1H, dd), 4.05 (2H1 s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
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Reference of 3335-98-6,Some common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, molecular formula is C14H11NO, 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 1Preparation of Compound 1 Sodium hydride (50% dispersion in mineral oil, 0.235 g, 4.8 mmol) was added to a stirred solution of 1,3-dihydro-1-phenyl-2H-indol-2-one 1a (2.0 g, 9.6 mmol) in dimethylacetamide (25 mL). To the resulting solution was added bis(2-chloroethyl)amine (1.7 g, 9.6 mmol) in benzene (25 mL) at room temperature. The resulting reaction was heated to about 50 C. and allowed to stir at this temperature for 0.5 hours, then additional sodium hydride (0.235 g, 4.8 mmol) was added and stirring was continued for 2 hours. The reaction mixture was cooled to room temperature, diluted with benzene and treated with water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to provide compound 1b.

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

Reference:
Patent; McCormick, Kevin D.; Aslanian, Robert G.; Mangiaracina, Pietro; Berlin, Michael Y.; De Lera Ruiz, Manuel; Boyce, Christopher W.; Chao, Jianhua; Ting, Pauline C.; Zheng, Junying; Rosenblum, Stuart B.; US2011/166124; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The synthetic route of 2-(4-Bromobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
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Electric Literature of 24566-79-8,Some common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
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Indoline | C8H9N – PubChem

Related Products of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

9.84 g (0.06 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dichloromethane under a nitrogen atmosphere, stirred at room temperature for about 10 minutes,11.8 g (0.12 mol) of cyclohexanone, 8.6 ml (0.15 mol) of acetic acid,29.7 g (0.14 mol) of sodium triacetoxy borohydride were added in this order, and the reaction solution was reacted at room temperature for 4 hours.200 ml of 1 N aqueous sodium hydroxide solution was slowly added to the reaction mixture, and the mixture was stirred for 30 minutes. The organic layer was separated, washed with H2O,The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting product was dispersed in 100 ml of methanol, stirred at room temperature for 30 minutes, filtered and dried to obtain 6-nitro-2,3-dihydro -1-cyclohexyl-1H-indole (55) (12.7 g, 86.0%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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. Recommanded Product: 480-91-1

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 480-91-1, its application will become more common.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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Related Products of 22190-33-6, The chemical industry reduces the impact on the environment during synthesis 22190-33-6, name is 5-Bromoindoline, I believe this compound will play a more active role in future production and life.

5-Bromoindoline (3.96 g, 20 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.69 g, 22 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1 N HCl solution (50 mL), a saturated NaHCO3 solution (2×50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. Trituration with hexane and drying in vacuo provided a white solid (2.26 g, 38% yield): 1H NMR (DMSO-d6, 300 MHz): 7.36 (s, 1H), 7.29 (d, 2H, J=7), 3.86 (t, 2H, J=7), 3.04 (t, 2H, J=7), 1.48 (s, 9H).

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

Reference:
Patent; Gilligan, Paul J.; US2006/63799; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Aminoisoindoline-1,3-dione

In a 2500 mL round bottom flask containing 0.62 mol (100 g) of 3-aminophthalimide, Add anhydrous ethanol 800mL, 455 mL of a methanol solution of KOH at a concentration of 80 g · L-1 (1 h addition, 0.65 mol KOH) was added dropwise with stirring. Continue stirring at room temperature for 3h, filter, The resulting white solid was rinsed with absolute ethanol, drying, The quality is 114g.

According to the analysis of related databases, 2518-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Plant Protection Institute; Mei Xiangdong; Si Weijie; Zhang Tao; Ning Jun; (17 pag.)CN104447498; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 340702-10-5, 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. 340702-10-5, name is 6-Fluoroisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C. suspension of 6-fluoroisoindoline-1-one (8.0 g, 5.3 mmol) in concentrated H2SO4 was added drop-wise a pre-cooled mixture of concentrated H2SO4 (26 mL) and nitric acid (6 mL) while keeping the reaction mixture below 5 C. After addition, the reaction mixture was slowly warmed to room temperature during overnight. Ice (50 g) was added to the mixture and the solid was collected and dried, then washed with MTBE (50 mL) and ethyl acetate (50 mL) to give the desired product as a light yellow solid (5.1 g, 50%). MS: (ES) m/z calculated for C8H6FN2O3[M+H]+ 197, found 197.

The chemical industry reduces the impact on the environment during synthesis 6-Fluoroisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); A1;,
Indoline – Wikipedia,
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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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

(a) 1-Methyl-5-nitroindoline. To a round-bottomed flask equipped with magnetic stirring was added 5-nitroindoline (0.82, 5.0 mmol, Aldrich), iodomethane (0.71 g, 5.0 mmol, Aldrich), sodium hydroxide (0.24, 6 mmol) and DMF (20 mL). The reaction mixture was stirred at 25 C. for 3 h, diluted with water (50 mL), extracted with EtOAc (3*40 mL) and the combined extracts were concentrated in vacuo. Purification by silica gel chromatography 97:3 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 179 (M+1).

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; Bo, Yunxin Y.; Chakrabarti, Partha P.; Chen, Ning; Doherty, Elizabeth M.; Fotsch, Christopher H.; Han, Nianhe; Kelly, Michael G.; Liu, Qingyian; Norman, Mark Henry; Ognyanov, Vassil I.; Wang, Xianghong; Zhu, Jiawang; US2003/195201; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem