Category: 3676-85-5

Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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 87 N’-(2-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Palladium hydroxide (one small spatula) was added to a solution of the crystal (100 mg, 0.29 mmol) of the compound prepared in Example 86 (mixed with 4-aminophthalimide) in DMF, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60min. 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. Methanol was added to the residue, followed by filtration to give the title compound as a crystal (27 mg, 29.7%). MS m/z: 310 1H-NMR delta: 4.19 (2H, d, J = 5.37 Hz), 5.09 (2H, s), 6.52 (1H, t, J = 7.32 Hz), 6.63 (1H, d, J = 7.32 Hz), 6.72 (1H, t, J = 5.73 Hz), 6.97 (1H, dt, J = 1.46, 7.56 Hz), 7.04 (1H, d, J = 7.56 Hz), 7.59 (1H, dd, J = 1.95, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 8.01 (1H, d, J = 1.95 Hz), 9.28 (1H, s), 11.08 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

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

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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6N2O2

EXAMPLE 8 The steps followed in the procedure of this example are illustrated diagrammatically below: STR6 Step (a), Production of 5-Aminophthalide Twenty grams of 4-aminophthalimide was added to a mixture of 41 gm zinc and 122 gm sodium hydroxide in 50 ml water (with good stirring) over 30 minutes. The mixture was stirred another 30 minutes, then heated to 60. When ammonia ceased to be evolved the mixture was heated for an additional 60 minutes, then cooled to about 30. The zinc residues were filtered off and the solution was acidified with 30 ml concentrated hydrochloric acid. The solution was heated to 90 for 45 minutes, then cooled and neutralized with 20 gm solid sodium carbonate, which brought the pH to 8-9. The product was filtered, washed with water and air dried. Wt=16.8 gm, m.p.=177-189.

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

Reference:
Patent; Pennwalt Corporation; US4665181; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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 stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

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

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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: C8H6N2O2

To 100 parts of nitrobenzene,4-aminophthalimide10 parts,And cyanuric chloride11 parts were added,And heated at 100 to 110 C. for 5 hours.After cooling it was filtered,Washed with methanol and water.And dried at 80 C. to obtain a compound represented by the formula (2)To obtain 17 parts of the intermediate (2) represented.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3676-85-5, its application will become more common.

Reference:
Patent; DAINICHISEIKA COLOR & CHEMICALS MANUFACTURING COMPANY LIMITED; IGUCHI, KAZUKI; YANAGIMOTO, HIROMITSU; (19 pag.)JP5823431; (2015); B2;,
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., Formula: C8H6N2O2

Commercially available 4-aminophthalimide (500 mg, 3.08 mmol) was dissolved in acetonitrile (15 mL). To the mixture were added cesium iodide (961 mg, 3.70 mmol), iodine (947 mg, 3.70 mmol), and copper iodide (712 mg, 3.70 mmol) at room temperature, and then an 11% aqueous hydrogen iodide solution (15 mL) and isoamyl nitrite (1.24 mL, 9.24 mmol) at 0C. The mixture was stirred at room temperature for 6.5 hours, and then for 1.5 hours after adding isoamyl nitrite (4.96 mL, 37.0 mmol). Then, saturated sodium bicarbonate was added to the mixture, and after filtration through sellite, the organic layer was separated. The resulting organic layer was washed with a saturated aqueous sodium thiosulfate solution and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was triturated with chloroform, and the resulting solid was filtered off and dried to give 4-iodophthalimido (394 mg, 47%). ESI-MS: m/z 272 [M-H]-.

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

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) in DMF (0.5 M) was stirred at room temperature up to 100 C until completion of the reaction (up to5 days). The reaction mixture was either diluted with EtOAc and the resultant precipitate filtered to give pure product or quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified either by automated flash chromatography (EtOAc:hexanes mixture) or by preparative HPLC to give the desired compound in 10-50% yield; ?H NIVIR (400 MHz, DMSO-d6)10.80 (s, 1H), 7.55 (dd, J= 13.2, 8.2 Hz, 3H), 7.48 – 7.40 (m, 1H), 7.15 (t, J 4.7 Hz, 1H), 7.03 (d, J 2.1 Hz, 1H), 6.97 (dd, J 8.4, 2.1 Hz, 1H), 4.53 (d, J= 4.6 Hz, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.07, 169.81, 154.14, 136.18, 135.86, 133.44, 131.11, 129.23, 125.00, 118.91, 115.96, 105.49, 43.32.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-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.

To a stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

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

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3676-85-5, 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.

Inthe above reaction scheme, the compound6and 7 was synthesized by literature procedure[2]. To a boiling ethanol solution (10 mL) of 7 (0.2 mmol, 30 mg) was added hydrazinehydrate 50% (0.2 mmol, 1 mL). Thereaction mixture was refluxed at 80 oC for 45 min. After completionof the reaction the reaction mixture was cooled in ice water bath, theprecipitate was collected and dried in room temperature. (Color: yellow solid;Yield: 25 mg (74%)). 1H-NMR spectrum of 8(DMSO-d6, 300MHz, ppm): delta 5.73 (s, 2H), 6.53 (s, 1H), 6.56 (s,1H), 7.30 (d, J = 8.4 Hz, 2H), 7.80 (s, 1H); 13C-NMRspectrum of 8 (DMSO-d6, 75MHz, ppm): delta 157.6, 154.3, 152.9, 128.8, 117.2, 119.3, 116.5, 106.0. 1 H-NMR spectrum of 7 (DMSO-d6,300 MHz, ppm): delta 5.54, (s 2H), 6.83 (dd, J = 6.1 Hz, 1H), 6.9 (d, J = 2.1 Hz, 1H), 7.48 (d, J = 8.4Hz, 1H), 7.58 (s, 1H), 10.24 (s, 1H).FTIR spectrum of 6, 7and8, FTIR (ATR)(nu,cm-1): 3317 (N-H), 1695 (C=O), 1543,1340 (N-O), 1070, 1301 (C-O), 715 (C-H); 3440 (N-H), 1710 (C=O), 1381, 1072 (C-O),746 (C-H) and 3740 (N-H), 1640 (C=O), 1407, 1072 (C-O), 719 (C-H),respectively. UV-Visible absorption of8(c 0.564¡Á10-4 mol/ L, C2H5OH); UV (C2H5OH)lambdamax(log epsilon) 273 (1.949).

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Daniel Thangadurai; Nithya; Rakkiyanasamy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 211; (2019); p. 132 – 140;,
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., SDS of cas: 3676-85-5

Example 250Preparation of rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)-amide To a stirred solution of thionyl chloride (2 mL), rac (2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (110 mg, 0.24 mmol) was added and the mixture was stirred at rt for 2 hrs. The excess thionyl chloride was removed and the residue was dissolved in methylene chloride (5 mL) and 5-amino-isoindole-1,3-dione (Aldrich, 0.30 mmol) was added followed by the addition of triethylamine (0.2 mL). The mixture was stirred overnight. The solvent was removed and the residue was purified on an ISCO machine (24 g column, eluent, 40-80% EtOAc/hexanes) to give a pale yellow solid. 10 mg.MS (ES+) m/z Calcd: [(M+H)+]: 611, found: 611

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

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., 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.