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.

General procedure: 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)

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:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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. Computed Properties of C8H6N2O2

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 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

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 104 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 305 mg (1.88 mM) of 4-Aminophthalimide in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100 C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80 C. to yield 348 mg of 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp=248-251 C.

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

Reference:
Patent; American Cyanamid Company; US6288082; (2001); 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Aminoisoindoline-1,3-dione

(a) 4-Methanesulfonamidophthalimide Methanesulfonylchloride (2.6 ml, 0.034 mol) was added dropwise to a stirred suspension of 4-aminophthalimide (5.0 g, 0.031 mol) in pyridine (50 ml). The mixture was stirred for 48 h under N2 at room temperature, after which time the solid formed was isolated by filtration, washing well with H2 O and CH2 Cl2 and then dried in vacuo to afford the subtitle compound as a colourless solid (5.67 g, 76%). Rf 0.52 (CH2 Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 241 (MH+).

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:
Patent; Pfizer Inc.; US6103738; (2000); A;,
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. Recommanded Product: 5-Aminoisoindoline-1,3-dione

General procedure: To a solution of substituted heteroaromatic amine (1.00 mmol) in dichloromethane, DMF or THF (2 mL) triethylamine (1.10 mmol) was added. The mixture was cooled in an ice bath and acryloyl chloride (1.05 mmol) was added dropwise. The reaction mixture was stirred for 24 hours at room temperature and extracted with water (3 × 3 mL). Subsequently, the aqueous layer was extracted with ethyl ether (3 × 5 mL). The combined organic layers were dried over anhydrous MgSO4 and filtered. After evaporation of solvents, the residue was purified on a silica column with chloroform:methanol mixtures (100:1, 50:1 v/v) as eluents to afford the respective acrylamides 10.

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; Kokosza, Kamil; Balzarini, Jan; Piotrowska, Dorota G.; Nucleosides, nucleotides and nucleic acids; vol. 33; 8; (2014); p. 552 – 582;,
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 98 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,3,4,5,6-pentafluorobenzyl)urea Diphenylphosphoryl azide (248 mg, 0.90 mmol, 1.2 eq) and triethylamine (91 mg, 0.90 mmol, 1.2 eq) were added to a solution of 2,3,4,5,6-pentafluorophenylacetic acid (158 mg, 0.75 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (59 mg, 0.75 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 (12 mg, 7.0%). MS m/z: 385 1H-NMR delta: 4.45 (2H, d, J = 5.12 Hz), 7.07 (1H, t, J = 5.98 Hz), 7.58 (1H, dd, J = 1.71, 8.05 Hz), 7.66 (1H, d, J = 8.05 Hz), 7.97 (1H, d, J = 1.95 Hz), 9.30 (1H, s), 11.09 (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

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.

Potassium hydroxide (0.415 g, 7.4 mmol) was added to a solution of 4-aminophthalimide (35) (1.00 g, 6.17 mmol) in dimethylformamide (50 ml) and the mixture was stirred at ambient temperature. After 2 hours, 4-trifluoromethylbenzylbromide (36) (1.9 mL, 12.34 mmol) was further added to the mixture and the mixture was stirred for another 18 hours. Water (100 ml) and ethyl acetate (100 ml) was added and the resulting phases separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient: 0-50 % ethyl acetate in cyclohexane) afforded Compound 37 as a yellow solid (0.750 g, 38 % yield): Rf= 0.2 (hexane/ethyl acetate 2:1 v/v). The Compound 37 (0.20g, 0.62 mmol.) was dissolved in dichloromethane (5 ml) and purged with argon. Benzyl chloroformate (0. lmL, 0.74 mmol) and triethylamine (0.60 mmol) were added to the amine solution and the resulting mixture was stirred for 2 hours at ambient temperature. After removal of the dichloromethane in vacuum, ethyl acetate (20 ml) and 10 % citric acid (20 ml) were added thereto and the resulting phases were separated. The organic phase was washed with 10 % sodium bicarbonate (20 ml) and brine (20 ml), dried over sodium sulfate and concentrated in vacuum. The residue was purified by chromatography on silica gel, and the resulting product was Compound 38. Compound 38,

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; TAIWANJ PHARMACEUTICALS CO., LTD.; YANG, Syaulan S.; LEE, Kuang Yuan; LIU, Meng Hsien; JIANG, Yan-Feng; FAN, Yu-Shiou; CHEN, Chi-Han; LIU, Sheng Hung; (94 pag.)WO2019/51222; (2019); 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. HPLC of Formula: C8H6N2O2

15 g of 5-aminophthalimide was added to 105 g of water and to this mixture, 39 g of a 35% aqueous hydrochloric acid was added dropwise. The reaction was kept at temperatures no higher than 5C and 48.7 g of a 16% aqueous sodium nitrite was added dropwise. Thereafter, the reaction was kept at temperatures from -2 to 2C for 120 minutes with stirring and the insoluble matter was removed by suction filtration to give an aqueous 5-diazophthalimide chloride.

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:
Patent; Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo; EP1650267; (2006); 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. Product Details of 3676-85-5

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 benzoylchloride and 1.20 mmol of triethylamine, then heated under reflux for 6 hours. After cooling, the solid that separates was collected by filtration, then dried under vacuum and purified by crystallization in ethanol. 250.3 mg of the desired product of the title were so obtained (yield 94%). It was characterized by chemical-physical and spectroscopical data. (0165) M.p. (C): >300. 1 H-NMR (delta, DMSO, d6): 7.649 (t, 1 H, Ar, J=7.25), 7.825 (t, 2H, Ar, J=7.69), 7.825 (d, 2H, Ar, J=8.32), 7.993 (d, 1 H, Ar, J=7.04), 8.145 (dd, 1 H, Ar, J=7.76, J=1.722), 8.331 (s, 1 H, Ar), 10.792 (s, 1 H, NH, exc), 11.269 (s, 1 H, NH, exc).

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; 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

Application of 3676-85-5, 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. 3676-85-5 name is 5-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.

Example 90 N-(2,6-Difluorobenzyl)-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 2,6-difluorophenylacetic 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 achloroform/methanol solution to give the title compound as a crystal (10 mg, 6.1%). MS m/z: 331 1H-NMR delta: 4.64 (2H, d, J = 4.64 Hz), 6.88 (1H, t, J = 5.73 Hz), 7.11 (2H, t, J = 8.05 Hz), 7.56 (1H, dd, J = 1.83, 8.29 Hz), 7.66 (1H, d, J = 8.29 Hz), 7.98 (1H, d, J = 1.71 Hz), 9.15 (1H, s), 11.08 (1H, s)

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