Category: 3676-85-5

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-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 3676-85-5, Recommanded Product: 3676-85-5

Example 88 N-(2,4-Dichlorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,4-dichlorophenylacetic acid (101 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with a chloroform/methanol solution to give the title compound as a crystal (9 mg, 5.0%). MS m/z: 363, 365 1H-NMR delta: 4.37 (2H, d, J = 4.88 Hz), 6.99 (1H, t, J= 5.22 Hz), 7.38 – 7.44 (2H, m), 7.57 – 7.63 (2H, m), 7.68 (1H, d, J = 8.29 Hz), 8.01 (1H, s), 9.46 (1H, s), 11.08 (1H, s)

The potential utility of systematic synthetic strategy will be applicable to efficient generations of chemical libraries of compounds to find ‘hit’ molecules.Read on for other articles about 3676-85-5.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5, Researchers are common within chemical engineering and are often tasked with creating and developing new chemical techniques, frequently combining other advanced and emerging scientific areas.

Example 82 N-(2-Chlorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (165 mg, 0.60 mmol, 1.2 eq) and triethylamine (61 mg, 0.60 mmol, 1.2 eq) were added to a solution of 2-chlorophenylacetic acid (85 mg, 0.50 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (81 mg, 0.50 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (37 mg, 22.6%). MS m/z: 329 1H-NMR delta: 4.40 (2H, d, J = 5.61 Hz), 6.94 (1H, t, J = 5.98 Hz), 7.28 – 7.38 (2H, m), 7.41 (1H, dd, J = 1.71, 7.56 Hz), 7.46 (1H, dd, J = 1.71, 7.56 Hz), 7.61 (1H, dd, J = 1.83, 8.17 Hz), 7.68 (1H, d, J = 8.54 Hz), 8.01 (1H, d, J = 1.46 Hz), 9.42 (1H, s), 11.08 (1H, s)

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Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application In Synthesis of 5-Aminoisoindoline-1,3-dione,The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.

The synthesis of bromoacetal 6 from phthalimide (7) is shown in FIG. 11. Based on reactions described in the literature, these transformations were carried out on large scale, and some steps were improved. Nitration of 200 g of phthalimide (7) gives 146 g of 5-nitrophthalimide (8). Reduction of 8 by catalytic hydrogenation, according to the literature procedure, is a bottleneck in the synthesis because of the large volume of solvent needed. With a 2 L Parr hydrogenator pressure vessel, 30 g of 8 is converted to 25 g of amine 9. The next step is also a reduction; aminophthalide 10 is obtained quantitatively from 9 by copper-catalyzed reaction with zinc in aqueous base. Steps b and c could be combined by treating 8 with zinc dust and copper(II) sulfate in 2 M aq. sodium hydroxide. This variation, which is not shown in FIG. 11, removes the bottleneck, potentially allowing 100 g of 10 to be prepared in one step from 146 g of 9. The reaction conditions for the steps shown in FIG. 11 are as follows: a) HNO3, H2SO4, 0 C., 56% ; b) 5% Pd/C, H2, EtOAc, 97% ; c) Zn, CuSO4, 6 M NaOH, 5 C. then heated at 70-80 C. 16 h, 100% ; d) NaNO2, 4 M HBr, followed by CuBr at 0 C.; e) DIBAL, toluene, -42 C.; f) BF3 OEt2, MeOH, RT.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Bell, Thomas W.; Cline, Joseph I.; Cremo, Christine R.; Gillett, Stephen L.; Frederick, John H.; US2011/77394; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 3676-85-5 as follows. name: 5-Aminoisoindoline-1,3-dione

Potassiumhydroxide (0.35 g,6.17 mmol) was added to a solution of 4-aminophthalimide 10 (1.00 g, 6.17 mmol) in dimethylformamide(30 mL) and the mixture was stirred at ambient temperature for 2 h. Iodomethane (0.88 g, 6.17 mmol) wasadded and it was stirred for another 18 h at the same temperature. Water (50 mL) and ethyl acetate (50 mL)was added and the resulting phases were separated. The organic phase was washed with brine, driedover sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient:0-100% ethyl acetate in cyclohexane) afforded the title compound 11a as a yellow solid (1.00 g, 92% yield):1H-NMR (DMSO-d6): delta = 7.46 (d, J = 8.24 Hz, 1H), 6.90 (d, J = 2.00 Hz, 1H), 6.77 (dd, J = 8.24 Hz, 2.00 Hz,1H), 6.42 (br. s, 2H), 2.94 (s, 3H) ppm. 13C-NMR (DMSO-d6): delta = 168.87, 168.57, 155.27, 135.10, 125.17,117.33, 116.84, 107.42, 23.83 ppm. MS (m/z): 177 [M+ H]+.

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; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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Indoline | C8H9N – PubChem

With the volume and accessibility of scientific research increasing across the world, it has never been more important to continue building the reputation for quality and ethical publishing we’ve spent the past two centuries establishing., Electric Literature of 3676-85-5

Example 89 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,3,6-trichlorobenzyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,3,6-trichlorophenylacetic acid (118 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (57 mg, 29.1%). MS m/z: 397, 399 1H-NMR delta: 4.63 – 4.66 (2H, m), 6.87 (1H, t, J = 5.24 Hz), 7.55 (1H, d, J = 8.54 Hz), 7.57 (1H, dd, J = 1.95, 8.05 Hz), 7.67 (2H, d, J = 8.54 Hz), 8.00 (1H, d, J = 1.71 Hz), 9.14 (1H, s), 11.09 (1H, s)

In the meantime we’ve collected together some recent articles in this area about 3676-85-5 to whet your appetite. Happy reading!

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-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 3676-85-5, Recommanded Product: 3676-85-5

At room temperature,In a 25mL reaction bottle,Join in order3-aminophthalic acid imide(0.5 mmol), diphenylphosphoryl (1 mmol),TEMPO (0.05 mmol), and tetrahydrofuran 48 mmol, 2 mL), mixed evenly,The reaction is then heated to 40 C.The reaction was stirred for 12 hours.After the reaction was completed by TLC, pure water was added.Then add ethyl acetate for 3 times.The extracts are combined and the extract is dried over anhydrous sodium sulfate.The extract was concentrated under reduced pressure in vacuo (0.08 Mpa) to dryness to afford crude material.Then rinse with a mixed eluent of 3:1 by volume of petroleum ether and ethyl acetate.Silica gel column flash column chromatography,Obtaining the product of Example 4o,It was 152 mg of a yellow solid, yield 70%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Qufu Normal University; Wei Wei; Huang Qiang; Lv Yufen; Liu Qishun; (20 pag.)CN109942627; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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. category: indolines-derivatives

Example 112 N-(3-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (182 mg, 0.66 mmol, 1.2 eq) and triethylamine (67 mg, 0.66 mmol, 1.2 eq) were added to a solution of 3-nitrophenylacetic acid (100 mg, 0.55 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (89 mg, 0.55 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 3 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with chloroform/methanol to give a nitro compound (45 mg, 24.1%) containing a minor amount of 4-aminophthalimide as the starting compound. DMF was added to the nitro compound (containing the starting compound, 40 mg, 0.12 mmol). Palladium hydroxide (one small spatula) was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure to give the title compound as a crystal (16 mg, 44.4%). MS m/z: 310 1H-NMR delta: 4.17 (2H, d, J = 5.37 Hz), 5.03 (2H, s),6.38 (1H, s), 6.44 (2H, d, J = 7.81 Hz), 6.51 (1H, s), 6.79 (1H, dd, J = 1.95, 8.05 Hz), 6.96 (1H, t, J = 7.68 Hz), 7.60 (1H, dd, J = 1.71, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 7.74 (1H, s), 8.03 (1H, d, J = 1.95 Hz), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

1.00 mmol of 5-aminoisoindoline-1 ,3-dione, commercial product, was solubilized in 1.0 ml_ of toluene and added with 1.20 mmol of commercial 4- chlorobenzoylchloride and 1.20 mmol of triethylamine, then heated at reflux for 10 hours. After cooling, the solid that separates was collected by filtration, dried under vacuum and purified by crystallization in methanol. 285.5 mg of the desired product of the title were so obtained (yield 95%). It was characterized by chemical-physical and spectroscopical data. M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 8.318 (d, 1 H, Ar, J=1.64), 8.131 (dd, 1 H, Ar, J=8.24, J=1.84), 8.024 (d, 2H, Ar, J=8.60), 7.838 (d, 1 H, Ar, J=8.16), 7.659 (d, 2H, Ar, J=8.61), 10.844 (s, 1 H, NH, exc), 1 1.272 (s, 1 H, NH, exc).

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; UNIVERSITA’ DI PISA; PAOLINI, Edoardo; QUATTRINI, Luca; COVIELLO, Vito; ANTONIOLI, Luca; FORNAI, Matteo; BLANDIZZI, Corrado; OH, Won Keun; LA MOTTA, Concettina; (30 pag.)WO2018/189679; (2018); 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C8H6N2O2

Example 314: Preparation of 5-((4-(cyclopropylamino)-5-(trifluoromethyl)pyrimidin-2- yl)amino)isoindoli -l,3-dione2-Chloro-N-cyclopropyl-5-(trifluoromethyl)pyrimidin-4-amine (0.060 g, 0.253 mmol) and 5-aminoisoindoline-l ,3-dione (0.041 g, 0.253 mmol) were mixed in acetic acid (2 ml). The mixture was microwaved at 120 C for 20 min and then concentrated. 1 mg of product was isolated after automated reverse phase chromatography (water-3% DMF in MeCN). MS calcd for [C16H12F3N502+H]+: 364.10, found 364.00.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Example 99 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,4,6-trifluorobenzyl)urea Diphenylphosphoryl azide (198 mg, 0.72 mmol, 1.2 eq) and triethylamine (73 mg, 0.72 mmol, 1.2 eq) were added to a solution of 2,4,6-trifluorophenylacetic acid (114 mg, 0.60 mmol) in toluene, and the mixture wasstirred at 110C for 60 min. Thereafter, 4-aminophthalimide (97 mg, 0.60 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (97 mg, 46.4%). MS m/z: 349 1H-NMR delta: 4.36 (2H, d, J = 4.64 Hz), 6.91 (1H, t, J = 5.73 Hz), 7.19 (2H, t, J = 8.66 Hz), 7.57 (1H, dd, J = 1.71, 8.05 Hz), 7.66 (1H, d, J = 8.29 Hz), 7.98 (1H, d, J = 1.71 Hz), 9.17 (1H, s), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem