Author: tianli

496-12-8, 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 496-12-8 as follows.

2) Triethylamine (0.33 ml, 2.37 mmol) and isoindoline (0.27 ml, 2.38 mmol) were added in turn to a solution of methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (820 mg, 2.25 mmol) in dimethyl sulfoxide (5 ml) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and ice water (50 ml) was added thereto. The mixture was stirred and the precipitates were filtered, washed with water and dried. The resultant yellow crystals were purified by column chromatography on silica gel (n-hexane/ethyl acetate=15) to give methyl ester of 5-chloro-2-(1,2,3,4-tetrahydroisoquinolinio)-3-nitrobenzoic acid (608 mg, 81%) as yellow crystals. m.p.: 114-115 C.; IR (Nujol) : 1743, 1705, 1603, 1589, 1529, 1503 cm-1; APCI-MS m/z: 333[M+H]+.

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

Reference:
Patent; J-Pharma Co., Ltd.; ENDOU, Hitoshi; WEMPE, Michael F.; PEYRON, Jean-Francois; ANZAI, Naohiko; JUTABHA, Promsuk; (83 pag.)EP2959918; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below.

General procedure: Acetone (150mL) and dibromoalkyl (30mol) were added to a 250mL three-necked round-bottom flask fitted with a mechanical stirrer and reflux condenser. Potassium phthalimide (11.85g, 10 mol) was added slowly over a 15-min period, and then the reaction mixture was heated under reflux for 10h. The reaction mixture was filtered via suction, and the acetone was removed via rotary evaporation. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:14) to afford 2-5 as white solid.

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; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, A common compound: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A solution of isatin (0.035 mmol, 1.2 equiv), tryptamine (0.03 mmol, 1.0 equiv) and (R)-3,3′-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (0.006 mmol, 0.2 equiv) was prepared in dry CH2Cl2 (0.06 M) at 25 C in an oven-dried and Ar-purged 4 mL vial fitted with a magnetic stir bar. The reaction was stirred until it was complete as judged by TLC (80% EtOAc/hexanes). The reaction was then concentrated and loaded onto a flash silica gel column (gradient of EtOAc/hexanes ending in 80% EtOAc/hexanes) to afford the spiroindolone product.

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; Badillo, Joseph J.; Silva-Garcia, Abel; Shupe, Benjamin H.; Fettinger, James C.; Franz, Annaliese K.; Tetrahedron Letters; vol. 52; 43; (2011); p. 5550 – 5553;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2518-24-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2518-24-3 name is 4-Aminoisoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

3-Aminophthalimide (2.00 g, 12.3 mmol) was dissolved in methanol (200 mL), and the solution was added with N-bromosuccinimide (2.19 g, 12.3 mmol), followed by stirring at room temperature for 50 minutes. The obtained solid was collected by filtration and washed with methanol to obtain 3-amino-6-bromophthalimide (2.21 g, yield 74%). APCI-MS m/z: 241 [M-H]-; 1H-NMR (DMSO-d6)delta(ppm): 6.53 (br s, 2H), 6.88 (d, J = 8.9 Hz, 1H), 7.49 (d, J = 8.9 Hz, 1H), 11.07 (br s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2108642; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8. 496-12-8

Example 66 Preparation of 2-(4-(2-(Isoindolin-2-yl)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one To a suspension of 2-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.50 g, 1.15 mmol) in anhydrous DMF (9 mL) was added isoindoline (0.41 mL, 3.46 mmol) and the reaction mixture was stirred at room temperature for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was triturated with water (50 mL). The separated solid was filtered, washed with water and ether, and dried under vacuum to give the title compound as a white solid. Yield: 0.45 g (83%). MP 202-202.5 C. 1H NMR (400 MHz, CDCl3): delta 10.09 (br s, 1H), 7.77 (s, 2H), 7.22 (br s, 4H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 4.11 (s, 4H), 4.03 (t, J=6.0 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.22 (t, J=6.0 Hz, 2H), 2.42 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Isoindoline.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-one, molecular formula is C9H9NO, 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. 61-70-1.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

The synthetic route of 1-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

675109-26-9, name is 6-Bromoisoindolin-1-one, 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. 675109-26-9

To a solution of 6-bromoisoindolin-l-one (2.418 g, 11.4 mmol) in DMF (57 mL) at 0 C. was added NaH (0.547 g, 13.68 mmol). The resulting dark suspension was allowed to stir for 60 min before addition of PMBC1 (1.86 mL, 13.68 mmol). The reaction was then allowed to stir at room temperature for 3 hours. The crude was diluted by EtOAc, washed with water and brine. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel using 0->50% EtOAc in hexanes to afford 3.18 g yellow solid as compound 2 (84% yield). 1H NMR (400 MHz, Chloroform-d) delta8.04 (d, J=1.9 Hz, 1H), 7.65 (dd, J=8.0, 1.9 Hz, 1H), 7.25 (d, J=8.6 Hz, 2H), 6.89 (d, J=8.6 Hz, 2H), 4.75 (s, 2H), 4.22 (s, 2H), 3.82 (s, 3H).

Statistics shows that 675109-26-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromoisoindolin-1-one.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; Wang, Guoqiang; He, Jing; Wang, Bin; Shen, Ruichao; Granger, Brett; Or, Yat Sun; US2019/62310; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 flame-dried screw-capped test tube equipped with a magnetic stir bar was added 1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane (0.396 g, 1.5 mmol), KF (0.087 g, 1.5 mmol) and 1- methylindoline-2,3-dione 3 (0.50 mmol). Then the screw-capped tube was evacuated and backfilled with argon. The mixture was dissolved in THF (2.0 mL) under argon atmosphere. The resultant reaction mixture was kept stirring at 30 C for 5 min. To the stirring solution was then added isoquinoline 1 (0.50 mmol) and the aryne precursor 2 (0.75 mmol). Then the reaction mixture was placed in preheated oil bath at 70 C. When TLC control showed the completion of the reaction (typically after 24 h), the reaction mixture cooled to room temperature and the solvent was evaporated and the crude residue was subsequently purified by flash column chromatography on silica gel to afford the corresponding spirooxazino isoquinoline derivatives (4) as an inseparable mixture of diastereomers in moderate to good yields. The dr was determined by 1H MR analysis of crude reaction mixture

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

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, Name is 1-Methylisatin, 2058-74-4, 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.

General procedure: A mixture of isatin derivative (1.0mmol), activated methylene (1.0mmol), 1,3-diketones (1.0mmol), and Fe3O4SiO2-imid-PMAn catalyst (0.8mol%) was stirred at 70C in water or irradiated in a microwave oven at 200W for an appropriate period of time as indicated in Table 2. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with hot ethanol (10mL). The catalyst was removed by using a magnetic field and then the solvent was evaporated and the pure product was obtained by recrystallization from ethanol.

Statistics shows that 1-Methylisatin is playing an increasingly important role. we look forward to future research findings about 2058-74-4.

Reference:
Article; Esmaeilpour, Mohsen; Javidi, Jaber; Divar, Masoumeh; Journal of Magnetism and Magnetic Materials; vol. 423; (2017); p. 232 – 240;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem