Category: indolines-derivatives

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0590] Procedure: To a stirred solution of 4-chloro-7-methoxyquinoline (0.05 g, 0.25 mmol) in 1,4- dioxane (5 mL) were added 5-nitroindoline (0.046 g, 0.28 mmol), cesium carbonate (0.25 g, 0.77mmol) and Xanthphos (0.029 g, 0.051 mmol). The resulting mixture was purged with argon for 15 min and added Pd2(dba)3 (0.023 g, 0.025 mmol) was added and the mixture was purged for another 10 min. Resulting mixture was stirred for 16h at 100 C. Progress of the reaction was monitored by TLC. Reaction mixture was filtered through celite bed and filtrate was diluted with ethyl acetate (20mL), washed with water (2 x 10mL) followed by brine (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified by combiflash using 55-60% ethyl acetate in hexane to afford 7-methoxy-4-(5-nitroindolin-1-yl)quinoline as yellow solid (0.12 g, 75%).1HNMR (400 MHz, DMSO-d6): delta 8.83 (d, J = 4.4 Hz, 1H), 8.08 (s, 1H), 7.91-(d, J = 8.8 Hz, 1H), 7.73 (d, J = 9.2 Hz, 1 H), 7.46 (s, 1H), 7.36 (d, J = 4.8 Hz, 1H), 7.23 (d, J = 9.2 Hz, 1H), 6.24 (d, J = 8.8 Hz, 1H), 4.26 (t, J = 8.4 Hz, 2H), 3.93 (s, 3H), 3.32 (t, J = 8.4 Hz, 2H); LCMS (ES) m/z = 322.1 [M+H]+.

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

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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.

To a 100 ml two-necked round bottom flask, 5.08 g phthalimide potassium salt (27.4 mmol) and 30 ml allylbromine (26.6 mmol) were dissolved in 40 ml DMF under the nitrogen atmosphere. The mixture was stirred for half an hour at 55 ¡ãC for 17 h, then 200 ml H2O was added and the mixture was?extracted with CH2Cl2 (80 ml ¡Á 3). The combined organic phase was dried over anhydrous Mg2SO4. After the removal of solvent under reduced pressure, the crude product was purified by column chromatography on silica gel with CH2Cl2 as the eluent, the collected pale?yellow oil was determined to be the desired product 2-allylisoindoline-1,3-dione (4.87 g, 95percent yield). 1H NMR (400 MHz, CDCl3): delta 7.90 (m, 2H), 7.76 (m. 2H), 5.93 (m, 1H), 5.26 (m, 2H), 4.34 (d, J = 8.0 Hz, 2H). 13C NMR (101 MHz, CDCl3): delta 167.95, 134.04, 132.26, 131.67, 123.37, 117.84, 40.14.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Potassium 1,3-dioxoisoindolin-2-ide, its application will become more common.

Reference:
Article; Wu, Huarui; Zheng, Chaoyue; Chen, Naiwu; Zhu, Jie; Gao, Deqing; Tetrahedron Letters; vol. 58; 16; (2017); p. 1576 – 1578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

(Intermediate Example 89) 3-Amino-1-(1,3-dihydroisoindol-2-yl)-3-methylbutan-1-one 2,3-Dihydro-1H-isoindole (543 mg) and 3-amino-3-methylbutanoic acid (700 mg) were dissolved in N,N-dimethylformamide (30 ml). N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (876 mg) and hydroxybenzotriazole (698 mg) were added thereto at 0C, and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic phase was separated, and the aqueous phase was adjusted to pH 9 by adding a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure to give the title compound (0.60 g, Y.: 60%) as a brown oily matter. 1H NMR; (CDCl3) delta (ppm): 1.2 (6H, s), 2.4 (2H, s), 4.7-4.8 (4H, m), 7.2-7.3 (4H, m). ESI/MS (m/z): 219 (M+H)+.

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 41663-84-7, 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 41663-84-7 as follows.

EXAMPLE 7 A first 2-l oil-jacketed reactor with a bottom valve was equipped with a mechanical stirrer, Dean-Stark trap topped with a reflux condenser, and nitrogen supply means. It was charged with 260.8 g (1.265 moles) of 4-nitro-N-methylphthalimide, 473 ml of ODCB and 25 g (95 mmol) of HEGCl (dried from a brine solution as described hereinabove). The solution was heated to reflux and 100 ml of ODCB was removed with a nitrogen sweep. A second, similarly equipped 2-l oil-jacketed reactor was placed under the first reactor and charged with 124 g (1.265 mole) of potassium acetate and 293 ml of ODCB. This mixture was heated and ODCB removed in the same way. The contents of the first reactor were transferred over 10 minutes, with stirring, to the second via a transfer tube, with maintenance of the temperature at 1 85 C. Refluxing was observed and colorless oxides of nitrogen evolved; they turned brown upon exposure to air. Heating and stirring were continued for 6 hours, after which the mixture was allowed to cool and solids were removed over 4 hours by suction filtration through a fritted funnel. The solids so removed were washed twice with 100-ml portions of water and vacuum dried at 140 C., yielding the desired 4,4′-oxybis(N-methylphthalimide) in 71% yield.

According to the analysis of related databases, 41663-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; General Electric Company; US6028203; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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 15362-40-0, Computed Properties of C14H9Cl2NO

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

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:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 110568-64-4, These common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-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.

Step 3: 5-aminoisoindolin-1-oneIron powder (2.51 g, 45 mmol), water (0.97 ml) and HCl (37%, 0.74 ml), were added to a stirred suspension of the 5-nitroisoindolin-1-one (800 mg, 4.5 mmol) from step 2 of this example in EtOH (11.2 ml). The mixture was heated at 95 C for 2h. Ammonia (7N in MeOH) was added (ImL) to make the pH of the mixture alkaline. The mixture was filtered to removed undissolved solids and the filter cake washed with EtOH (2×40 ml). The filtrate and organic washes were combined and concentrated in vacuum to give the titled compound.

Statistics shows that 6-Nitroisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 110568-64-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., COA of Formula: C8H4N2O4

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

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; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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. COA of Formula: C9H6BrNO2

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 39755-95-8, The chemical industry reduces the impact on the environment during synthesis 39755-95-8, name is 5-Methoxyisatin, I believe this compound will play a more active role in future production and life.

General procedure: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

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

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 147149-84-6, name is 4-Bromo-5-methylindoline-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 147149-84-6, Product Details of 147149-84-6

A mixture of 3N NaOH (80 ml, 79.15 mmol) and 4-bromo-5-methyl-lH-indole-2,3-dione (19 g, 79.15 mmol) was heated at 80C. To the solution was added hydrogen peroxide (18 ml, 176.22 mmol) slowly and the mixture was stirred for 1 hour and the mixture cooled to 5C then acidified to pH5 with concentrated HCI. The solution was evaporated to dryness and methanol (100 ml) then added. The mixture was filtered and the filtrate was evaporated to yield 6-amino-2-bromo-3-methylbenzoic acid (18 g, 99%) as brown solid. 1H NMR (400 MHz, DMSO, 30C) 2.21 (3H, s), 6.71 (1H, d), 7.07 (1H, d). Three exchangeable protons not observed m/z: ES+ [M+H]+ = 230.

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, 4-Bromo-5-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; LAMONT, Scott, Gibson; KEMMITT, Paul, David; GOLDBERG, Frederick, Woolf; (158 pag.)WO2019/215203; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem