Category: 3416-57-7

Electric Literature of 3416-57-7, These common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-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.

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

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

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(2-Oxopropyl)isoindoline-1,3-dione

EXAMPLE 1 Phthalimidoacetone ethylene ketal A solution of phthalimidoacetone 61.9 g (300 mmole) and ethylene glycol 18.9 g (300 mmole) in 300 ml of benzene in the presence of concentrated sulfuric acid (1 drop) is refluxed with stirring for 24 hours. An additional portion of ethylene glycol (18.9 g., 300 mmole) and p-toluenesulfonic acid (3 mg) is added and refluxing is continued for 65 hours. The reaction mixture is cooled in ice, washed with saturated sodiumchloride solution and dried over anhydrous sodium sulfate. The benzene is removed in vacuo and the residue is crystallized from methanol to give 67 g (90%) of phthalimidoacetone, ethylene ketal as white prisms of melting point 92-94 C.

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

Reference:
Patent; The Upjohn Company; US3992408; (1976); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

5.4. Example 4; To a solution of powdered LiOH (17.25 g, 1.5 eq) in anhydrous methanol (600 ml) was added cyanoacetamide (63 g, 1.5 eq) under nitrogen atmosphere. The resulting mixture was stirred for 20 min at room temperature. To this was added a solution of phthalimidoacetone (101.5 g, 0.5 mol) in 700 ml of THF (anhydrous) over a period of 30 min. Resulting reaction mixture was stirred for 2 h at room temperature and then heated at 55 C. for 1 h. To this was added sodium methoxide solution (25% solution, 172 ml, 1.5 eq) at 55 C. over a period of 40 min. After 3 h HPLC/MS indicated starting material and intermediates were converted to 2-amino-4-methyl-1H-pyrrole-3-carboxamide. To this reaction mixture was added ethyl formate (200.8 ml, 5 eq) over a period of 20 min followed by sodium methoxide (25% solution, 324 g, 3 eq). The resulting reaction mixture was heated for 7 h at 55 C. at which time HPLC/MS indicated that the intermediate pyrrole compound was converted to the final product. The reaction mixture was diluted with 1.5 L water, heated at 60 C. for 1 h, and then concentrated to small volume (11.5 L). Solution assay indicated that final product was formed in 75% solution yield. This solution was acidified to pH 7.5 with 6 N aq. HCl, cooled to about 5 C., and held at this temperature for 30 min. The solid was filtered, washed with water, dried at 50 C. under vacuum overnight to give the final product as a light brown solid (45.8 g, 61% yield, purity: 99.0% by HPLC area).

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

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature 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.

2.0g of compound I is mixed with 3.76g of potassium carbonate thoroughly, then the resulting mixture is poured into a 25ml flask followed by adding 4.0ml of chloroacetone into, heating the solution to 90-110C (a reflux condensing tube is needed to be equipped on the flask, the system is protected with argon) while stirring, maintaining the temperature, and conducting the reaction for 3-4 hours. After the reaction is completed, excess chloroacetone is removed under a reduced pressure, into the residue is added a great deal of water, then filtrated with Buchner’s filter. The resulting solid is washed twice with 10ml of 10% NaOH and 5-6 times with water respectively, dried under vacuum to obtain compound II; After a reflux condensing tube and a dropping funnel are connected on a three-necked bottle, 100ml of absolute methanol (or other anhydrous solvent) is added into the three-necked bottle, followed by slowly adding 0.23g of metallic sodium (or directly adding 10mmol of sodium methoxide). After the solid dissolves entirely, the solution is heated and refluxed, then compound II dissolved in absolute methanol (60ml CH3OH and 1.0g compound II) is dropped into by dropping funnel. After conducting the reflux for 2 hours the reaction is processed as follows: cooling the system with icewater bath, slowly neutralizing the reaction solution with 1M hydrochloride, continuing to stir for 30min in icewater bath after a large amount of solid emerge, filtrating to obtain a solid, then washing the solid with small amount of water, drying in vacuum, thereby obtaining compound III. 230mg of compound III is placed in a 25ml flask followed by adding 5ml solvent (listed in the above) into, air is blown into by a bubbler continuously. The reaction is completed after 10 hours and processed as follows: diluting the reaction solution with 30ml of acetic ether, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, the residue is applied on silica gel column (petroleum ether: acetic ether=2:1) to obtain compound IV

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

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; EP1640367; (2006); 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A solution of 123 g of pyridinium bromide perbromide in 600 ml of THF was slowly added dropwise to 2-(2-oxopropyl)-1H-isoindole-1,3 (2H)-dione (70 g; 0.345 mol) in 600 ml of THF, and the mixture was then stirred for about 3 h. For workup, the precipitated solids were filtered off, and the mother liquor was concentrated, taken up in ethyl acetate and thoroughly washed with aqueous bisulfite solution. Drying and concentration afforded 150 g of a yellow oil, which was stirred with methyl tert-butyl ether. 63.4 g; m.p.: 142 to 143 C.; ESI-MS [M+H+]=283.95

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

Reference:
Patent; Abbott GmbH & Co. KG; US7105508; (2006); B1;,
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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H9NO3

Compounds 19 and 20 were synthesized by a method similar to that illustrated in paragraph [0313] above except that the starting compound was 2-(2-oxopropyl)isoindoline- 1,3-dione. [0340] Synthesis of 3-((l,3-Diphenyl-lH-pyrazol-5-yl)amino)isonicotinic acid

According to the analysis of related databases, 3416-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; (178 pag.)WO2016/44666; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of l-[4-(trifluoromethyl)phenyl]methanamine (1.7 g, 9.7 mmol, 1.5 equiv) in trifluoroethanol (10.0 mL) was added 2-(2-oxopropyl)isoindoline-l,3-dione (2.0 g, 9.6 mmol, 1.5 equiv). After stirring at r.t. for 10 min, to the mixture was added 5-chloro-3- fluoro-2-isocyanopyridine (1.0 g, 6.4 mmol, 1.0 equiv) and chloroacetic acid (899.4 mg, 9.5 mmol, 1.5 equiv). The resulting mixture was stirred at 60 C overnight, concentrated under vacuum, and purified by C18 column, eluted with water (0.5%NH4HCO3)/ACN (1/5) to afford 750 mg of /V-(5-chloro-3-fluoropyridin-2-yl)-2-(2-chloro-/V-[[4- (trifluoromethyl)phenyl]methyl]acetamido)-3-(l,3-dioxoisoindol-2-yl)-2-methylpropan amide (Intermediate 64-2) as a yellow oil. LRMS (ES) m/z 611 (M+H).

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

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C11H9NO3

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use.1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)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 3416-57-7, Recommanded Product: 3416-57-7

5.3. Example 3; Cyanoacetamide (62 g, 1.5 eq) and powdered lithium hydroxide (18 g, 1.5 eq) were mixed in 500 ml DMF and it was stirred at room temperature for 30 min. To the mixture was added a solution of phthalimidoacetone (100 g, 0.49 mol, purchased from TCI America, Portland, Oreg., USA, or prepared according to Lei, et al, J. Am. Chem. Soc. 2004, 126, 1626) in DMF (200 ml) over 1 h at room temperature. Additional DMF (25 ml) was used as a rinse. After stirring at room temperature for 5 min, HPLC/MS showed formation of the adol compound (MS: MH+=222.1, MNa+=244.0). Methanol (50 ml) was added followed by 25% sodium methoxide solution (160 g, 1.5 eq) and methanol rinse (50 ml). This mixture was heated at 60-65 C. for 2 h to form 2-amino-4-methyl-1H-pyrrole-3-carboxamide. To this reaction mixture was added ethyl formate (100 ml, 2.5 eq) at 40-60 C. After stirring for 15 min, more methanol (50 ml) was added followed by simultaneous addition of ethyl formate (100 ml, 2.5 eq) and 25% sodium methoxide solution (266 g, 2.5 eq) over 30 min. Additional methanol (50 ml) was added as rinse. The resulting mixture was heated at 60 C. for 5 h. More 25% sodium methoxide solution (113 ml, 1 eq) was added, and heating continued for 1 h more to convert all of the pyrrole N-formyl intermediate (MS: MH+=151.1). Water (400 ml) was added and mixture was heated at 60 C. for 30 min. Solution assay indicated the final product was formed in 69% yield. The hydrolyzed reaction mixture was concentrated under vacuum and diluted with water (1000 ml). The pH was adjusted to about 7.6 with 6 N HCl at 60-65 C. The resulting slurry was heated at 60-65 C. for 15 min and cooled slowly to 10 C. The solids were filtered, washed with water, and dried at 50-60 C. under vacuum. The final product was obtained as a light purple solid (39.5 g, 54% yield, purity: 99.8% by HPLC area).; 5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

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; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., 3416-57-7

(Synthesis of Intermediate 3)102 g (0.5 mol) of the intermediate 1 and 147 g (0.5 mol) of the intermediate 2 thus obtained were mixed with 500 ml of ethanol, and the mixture was stirred while cooled to 5 C. to 10 C. 201 ml of SM-28 (28% sodium methoxide methanol solution) was added dropwise to the dispersion. The temperature of the reaction solution was kept to 10 C. or lower. After dropwise addition, the mixture was allowed to warm to room temperature and stirred additionally for 30 minutes, and then, after addition of 20 ml of water, stirred as heated under reflux additionally for 4 hours. After reaction, the reaction solution was cooled to room temperature, and 750 ml of water was added dropwise, allowing precipitation of the crystal. The crystal was filtered, washed with water and dried. The crystal was washed ad dispersed and stirred in 1,000 ml of n-hexane, filtered and dried, to give 143 g of an intermediate 3 (yield: 82.2%).

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; FUJIFILM CORPORATION; US2012/238752; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem