Month: June 2021

These common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-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. Formula: C9H7NO3

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).

The synthetic route of 6-Methoxyindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Compound VII: Weigh 2.3g o-nitrobenzyl mercaptan (14.2mmol) And 5.73g of N-(2-bromoethoxy)phthalimide (21.3mmOl) in a round bottom flask, Dissolved with 25ml dimethyl sulfoxide, To the reaction solution was added 3ml of triethylamine (21.3mmol), and reacted at room temperature for 4h; TLC monitoring showed that o-nitrobenzyl mercaptan was completely consumed. To the reaction mixture, an appropriate amount of water was added and the mixture was extracted with dichloromethane for 2-3 times. The organic phase was collected, dried over anhydrous sodium sulfate, Separation by column chromatography (RhoEpsilon:EpsilonAlpha = 5:1), 3.74 g of compound VII (N- (2 – ((2-nitrobenzyl) mercapto) ethoxy) phthalimide was obtained as a white solid (73.2% yield). As shown in FIG. 4, FIG. 4 is a nuclear magnetic hydrogen spectrum of the compound YPi11 prepared in this example.

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

Reference:
Patent; University of Science and Technology of China; Huang Jianfeng; Shi Jing; Chu Guochao; (21 pag.)CN107698474; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)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 5332-26-3, category: indolines-derivatives

Example 1 Diphenyl(phthalimidomethyl)phosphine oxide IV Toluene (25 ml) was added to a mixture of ethyl diphenylphosphinite (5 g, 21.71 mmole) and the N-(bromomethy)phthalimide III (5.21 g, 21.70 mmole) at room temperature. The reaction mixture was heated to 90 C. and maintained at this temperature for 48 h when the reaction was complete as indicated from the TLC of the reaction mixture. The reaction mixture was concentrated under reduced pressure, triturated with toluene and filtered to furnish the phosphine oxide compound IV as a solid; yield: 6 g, 76.5%.

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; HELVETICA INDUSTRIES (P) LIMITED; US2011/263870; (2011); A1;,
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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C13H18N2O2

Part H. To tert-butyl-5-amino-1-indolinecarboxylate (1.90 g, 8.2 mmol) was added 5-bromovaleryl chloride (1.4 mL, 9.0 mmol) and 18 mL of THF. After stirring for 5 min at rt under N2, potassium tert-butoxide (9 mL, 9 mmol; 1.0 M in THF) was added in one portion, and the resulting brown solution was stirred under N2 for 30 min. A second portion of potassium tert-butoxide (9 mL) was added, and the resulting brown suspension was stirred for 15 min. An additional 0.10 mL-portion of 5-bromovaleryl chloride and a 4.5 mL-portion of potassium tert-butoxide were added, and the mixture was stirred for 30 min. The reaction was then poured into H2O (80 mL). The aqueous layer was washed with EtOAc (3*50 mL), and the combined organic layers were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated and the resulting residue was purified by radial chromatography (50% EtOAc in hexanes) to afford tert-butyl 5-(2-oxo-1-piperidinyl)-1-indolinecarboxylate as a pink solid (1.30 g, 50%). LRMS (AP+): 317.2 (M+H)+. 1H NMR (CDCl3) delta 7.40-7.80 (br m, 1H), 7.01 (s, 1H), 6.97 (d, 1H), 3.94 (t, 2H), 3.55 (br m, 2H), 3.09 (t, 2H), 2.49 (br m, 2H), 1.91 (br m, 4H), 1.52 (s, 9H).

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; Bristol-Myers Squibb Company; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; (132 pag.)US2017/50964; (2017); A1;,
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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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Safety of Isoindoline

General procedure: To a mixture of tert-butyl-3-bromopropylcarbamate 1.2 (5.6mmol, 1.3 eq, 1.3g) and N,N-disubstituted amine (4.3mmol, 1 eq) in 30mL of DMF was added potassium carbonate (13.0mmol, 3 eq, 1.8g). The resulting mixture was heated at 70C for 24h. Then, the solvent was removed under reduced pressure and water (80mL) added to the residue. The crude product was extracted with 3×60mL of DCM. The combined organic fractions were washed with 60mL of water and dried over magnesium sulphate. The solvent was evaporated and the crude product collected as yellow oil. Purification by column chromatography (DCM: MeOH(NH3), 9.7:0.3 (v/v)) was performed.

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; Donnier-Marechal, Marion; Carato, Pascal; Larchanche, Paul-Emmanuel; Ravez, Severine; Boulahjar, Rajaa; Barczyk, Amelie; Oxombre, Benedicte; Vermersch, Patrick; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 964 – 978;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 337536-15-9, These common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, 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.

The compound II obtained in Example 3 was dissolved in 2 L of THF. Cool down to 0 C, Sodium borohydride 2.5 eq was added in four batches. After the stirring is stable, Add boron trifluoride etherate 2.0 eq, The temperature was further raised to 70 C and refluxed for 8 hours. TLC tracking. Cool down to 0 C, The reaction was quenched by dropwise addition of methanol. Then add 6M hydrochloric acid, Adjust the pH to 3-4, The temperature was further raised to 70 C and refluxed for 8 hours. Cool to room temperature, filter, Mother liquor is concentrated, Get the product hydrochloride.

Statistics shows that 4-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 337536-15-9.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

10.0 g (0.061 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dimethylformamide under nitrogen atmosphere, stirred for about 10 minutes at room temperature and then dissolved in 2-bromoethyl 15.3 g (0.01 mol) of ether and 15.0 ml (0.088 mol) of diisopropylethylamine (DIPEA) were added in this order. The reaction solution was gradually heated and stirred at 140 C for 5 hours to complete the reaction. After cooling the reaction solution to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate, The resulting product was purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 1: 3) to obtain 6-nitro-2,3-dihydro-1- (2-ethoxyethyl) 12.0 g (83.3%) of indole (43) was obtained.

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

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

Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)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 446292-08-6, Computed Properties of C22H19N3O6

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%)

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; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, name is 7-Fluoroisatin, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 7-Fluoroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., name: 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem