Author: Jessica.F

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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5394-18-3

General procedure: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

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; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
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Synthetic Route of 3416-57-7,Some common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, molecular formula is C11H9NO3, 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.

Reference Example 27 Methyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-methylbut-2-enoate A solution of methyl dimethylphosphonoacetate (21.5 g) in N,N-dimethylformamide (50 mL) was added dropwise to a suspension of sodium hydride (63%, 4.50 g) in N,N-dimethylformamide (100 mL) with stirring at 0 C. The mixture was stirred at 0 C. for 30 minutes. Then, a solution of phthalimidoacetone (20.0 g) in N,N-dimethylformamide (50 mL) was added dropwise thereto, and the mixture was heated to room temperature and stirred overnight. To the reaction solution, water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and saturated sodium chloride solution and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained crude product was purified by silica gel column chromatography to obtain the title compound (20.6 g). 1H-NMR (CDCl3) delta: 1.78-1.79 (0.9H, m), 2.21-2.22 (2.1H, m), 3.67 (2.1H, s), 3.75 (0.9H, s), 4.31-4.32 (1.4H, m), 5.03-5.03 (0.6H, m), 5.66-5.67 (0.7H, m), 5.86-5.88 (0.3H, m), 7.72-7.78 (2H, m), 7.85-7.91 (2H, m).

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; Nagata, Tsutomu; Kobayashi, Jun; Onishi, Yoshiyuki; Kishida, Masamichi; Noguchi, Kengo; US2013/12532; (2013); A1;,
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Indoline | C8H9N – PubChem

Application of 2058-72-2, The chemical industry reduces the impact on the environment during synthesis 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a hot solution of 4-hydrazinylbenzenesulfonamide 2 (0.22 g,1.2 mmol) in acetic acid (15 mL), the appropriate isatin derivative 3a-c or 6a-o (1.2 mmol) was added. This mixture was heated under reflux for 6 h. The formed precipitate was filtered off while hot and washed with ethanol and petroleum ether then recrystallized fromDMF/ethanol to obtain the target compounds 4a-c and 7a-o,respectively, in 52-87% yield.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Bonardi, Alessandro; Bua, Silvia; Ibrahim, Hany S.; Elaasser, Mahmoud M.; Kry?tof, Vladimir; Jorda, Radek; Gratteri, Paola; Abou-Seri, Sahar M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 184; (2019);,
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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 446292-08-6 as follows. category: indolines-derivatives

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-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 17702-83-9, Computed Properties of C16H20BrNO2

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained.

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-(8-Bromooctyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-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 324-03-8, category: indolines-derivatives

To a stirred solution of starting material E-1.1-6 (55.0 g; 333.1 mmol) in DMF (550 ml_) is added K2CO3 (55.2 g; 399.7 mmol) and 2-iodo-propane (73.6 g; 433.0 mmol) at 25 C. The reaction mixture is stirred at 25 C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer is concentrated under reduced pressure to obtain crude compound. The crude is purified by column chromatography using silicagel (230-400 pm) with eluting mixture of ethyl acetate and hexane. Yield: 51 % (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method RND-FA-4.5-MIN

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 21857-45-4, These common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, 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 2: To a solution of 3-(4-nitro-1 H-pyrazol-1-yl)propanal (200 mg, 1 .18 mmol) in MeOH (12.0 mL), 5-methoxyindoline (176 mg, 1 .18 mmol) was added. This reaction mixture was stirred at rt for 1 h, then NaBH4 (121 mg, 3.20 mmol) was added and stirred for another 30 min at rt. The reaction mixture was quenched with water and extracted with EtOAc (2x). The combined org. layers were dried (MgS04), filtered and the solvent was removed under reduced pressure to yield 5-methoxy-1-(3-(4-nitro-1 H-pyrazol-1 -yl)propyl)indoline, which was used in the next step without further purification. LC-MS conditions B: tR = 0.56 min, [M+H]+= 303.15.

Statistics shows that 5-Methoxyindoline is playing an increasingly important role. we look forward to future research findings about 21857-45-4.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-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 324-03-8, Quality Control of 6-Fluoroindoline-2,3-dione

General procedure: Similar to as described in General Procedure Z, 6-fluoro-2,3-dihydro- 1H-indole-2,3-dione was converted to the title compound as a yellow solid (ig, 15%). LC-MS (ES, iWz): 195 [M+H]; A solution of 2,3-dihydro-1H-indole-2,3-dione (1 eq.) and sodium hydroxide (1.1 eq.) in water was stirred for 5-30 mm at 25 C. Then a solution of sodium nitrite (1 1 eq.) in water and concentrated sulfuric acid (2 eq.) were added dropwise with stirring at 0.-10 C. After 5-30 mm a solution of SnC12 (2.5 eq.) in concentrated hydrochloric acid (15-30 eq.) was added slowly. After5 being stirred for 1–5 h at 25 C the reaction mixture was filtered and the solid was dissolved in methanol. Sulfuric acid (0.5-1 eq.) was added to the solution and the solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum to give the ester which may need further purification such as fresh chromatography.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 126674-93-9, name is 4,6-Difluoro-1H-indole-2,3-dione, molecular formula is C8H3F2NO2, 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. Application In Synthesis of 4,6-Difluoro-1H-indole-2,3-dione

Stage 3: 2-amino-4,6-difluorobenzoic acid First sodium hydroxide (6.70 g, 167 mmol) and then 30% hydrogen peroxide (6.7 ml) in water (60 ml) were added to a suspension of the product from stage 2 (4.58 g, 25 mmol) in water (125 ml) at 0 C. The mixture was stirred at room temperature for 20 h and then brought to pH 3 with formic acid (approx. 11 ml, severe foaming), during which the title compound precipitated out. The mixture was then filtered and product was dried over phosphorus pentoxide in a desiccator. Yield: 3.72 g (86%), white solid. Melting point: 198-202 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 126674-93-9, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 61-70-1, 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 61-70-1 as follows.

N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58% yield.1H-NMR (300MHz, CDCl3) delta(ppm) : 7.42-7.39 (d, 1H), 7.26 (s, 1H), 6.71-6.68 (d,1H), 3.52-3.20 (s, 2H), 3.19 (s, 3H).

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
Indoline – Wikipedia,
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