Category: 3676-85-5

Electric Literature of 3676-85-5, The chemical industry reduces the impact on the environment during synthesis 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

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 field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Aminoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Related Products 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.

To a solution of intermediate compound 3 (0.037 mol) in 20 ml of concentrated hydrochloric acid was added slowly to a solution of sodium nitrite (0.039 mol) in 15 ml of water under ice-cooling. The temperature of the control solution was not more than 5 C. After adding, the mixture was stirred for 30 minutes under ice bath, and the insoluble matter was filtered off. The filtrate was slowly added to a mixture of cuprous chloride (0.3737 mol) in 10 ml of concentrated hydrochloric acid, stirred and added at 70 C until no more bubbles were allowed to stand for 12 hours, filtered to give a yellow solid,The filter cake was washed with water and recrystallized from ethanol to give intermediate 4 as a yellow solid in 58.6% yield

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; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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 76 N-Cyclohexylmethyl-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (232 mg, 0.85 mmol, 1.2 eq) and triethylamine (85 mg, 0.85 mmol, 1.2 eq) were added to a solution of cyclohexylacetic acid (100 mg, 0.70 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (114 mg, 0.70 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 150 min. After the completion of the reaction, the reaction solution was poured into water, 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. The residue was purified by a preparative TLC [chloroform-acetone] to give the title compound as a crystal (46 mg, 21.7%). MS m/z: 301 1H-NMR delta: 0.85 – 0.96 (2H, m), 1.07 – 1.26 (3H, m), 1.35 – 1.47 (1H, m), 1.58 – 1.73 (5H, m), 2.97 (2H, t, J = 6.22 Hz), 6.42 (1H, t, J = 5.73 Hz), 7.56 (1H, dd, J = 1.95, 8.29 Hz), 7.66 (1H, d, J = 8.30 Hz), 8.01 (1H, d, J = 1.71 Hz), 9.11 (1H, s), 11.06 (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

Related Products 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.

Preparative Example 1 4-Cyanophthalimide STR16 4-Aminophthalimide (40.0 g) was suspended in 300 ml of water, followed by the addition of 57 ml of concentrated hydrochloric acid. The obtained suspension was stirred under cooling with ice. A solution of 20.6 g of sodium nitrite in 69 ml of water was dropped into the above suspension at a bulk temperature of 5 C. or below. The obtained mixture was cooled to -20 C., followed by the addition of 300 ml of toluene. The resulting mixture was adjusted to pH7 with sodium hydrogencarbonate under vigorous stirring to form a diazonium salt. Separately, a solution of 105.7 g of potassium cyanide in 206 ml of water was dropped into a suspension of 63.4 g of cuprous chloride in 250 ml of water, while the suspension was vigorously stirred under cooling with ice. The obtained mixture was further stirred under cooling with ice for one hour, followed by the addition of 500 ml of ethyl acetate. The diazonium salt prepared above was added into the resulting mixture in several portions and the obtained mixture was stirred under cooling with ice for one hour. The resulting mixture was filtered through Celite to remove insolubles and the Celite was washed with an ethyl acetate/tetrahydrofuran mixture. The filtrates were together left standing to cause liquid-liquid separation. The organic phase was washed with a saturated aqueous solution of sodium hydrogen-carbonate, dilute hydrochloric acid and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by vacuum distillation. The title compound (41 g) was obtained as a reddish-brown solid. M.p.: 237.0-238.0 C.; MASS: 173 (MH+); 1H–NMR (400 MHz, DMSO-d6) delta: 8.00(1H, dd, J=7.5, 1.0 Hz), 8.29(1H, dd, J=7.5, 1.5 Hz), 8.36(1H, dd, J=1.5, 1.0 Hz), 11.73(1H, s)

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

Reference:
Patent; Eisai Co., Ltd.; US5849741; (1998); A;,
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., Recommanded Product: 5-Aminoisoindoline-1,3-dione

Example 86 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2-nitrobenzyl)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-nitrophenylacetic acid (90 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, was washed with ethyl acetate, and was further washed with a chloroform/methanol solution to give the title compound as a crystal (11 mg, 6.5%). MS m/z: 340 1H-NMR delta: 4.61 (2H, d, J = 5.37 Hz), 7.00 (1H, t, J = 5.73 Hz), 7.53 – 7.70 (4H, m), 7.76 (1H, t, J = 7.44 Hz), 8.00 (1H, s), 8.06 (1H, d, J = 7.44 Hz), 9.48 (1H, s), 11.09 (1H, s)

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; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
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.

A mixture of 4-aminophthalimide (0.62 mmol), 2,6-dichlorophenylisocyanate (0.62 mmol), and DMF (cat.) in toluene (3 mL) was heated at 105 C for 19 h. The reaction mixture was concentrated and the crudematerial was purified via preparative HPLC to give compound 117 in 1% yield. ?H NMR (400MHz, DMSO-d6) 11.15 (s, 1H), 9.78 (s, 1H), 8.60 (s, 1H), 8.05 (t, J 1.2 Hz, 1H), 7.73 (d, J1.2 Hz, 2H), 7.57 (d, J= 8.1 Hz, 2H), 7.36 (t, J= 8.1 Hz, 1H). ?3C NIVII{ (101 1VIHz, DMSO)169.63, 169.49, 152.71, 146.11, 134.78, 134.62, 133.35, 129.33, 129.00, 125.49, 124.55, 122.71,111.96.

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

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., Recommanded Product: 5-Aminoisoindoline-1,3-dione

Example 109 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,3,6-trifluorobenzyl)urea Diphenylphosphoryl azide (173 mg, 0.63 mmol, 1.2 eq) and triethylamine (64 mg, 0.63 mmol, 1.2 eq) were added to a solution of 2,3,6-trifluorophenylacetic acid (100 mg, 0.53 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (85 mg, 0.53 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 to give the title compound as a crystal (100 mg, 54.6%). MS m/z: 349 1H-NMR delta: 4.43 (2H, d, J = 5.37 Hz), 6.98 (1H, t, J = 5.86 Hz), 7.11 – 7.18 (1H, m), 7.40 – 7.50 (1H, m), 7.58 (1H, dd, J = 1.83, 8.05 Hz), 7.66 (1H, d, J = 8.05 Hz), 7.98 (1H, d, J = 1.46 Hz), 9.21 (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

Reference of 3676-85-5, 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.

A mixture of 4- aminophthalimide (1 .2 mmol), 2,6-dichlorobenzenesulfonyl chloride (1 .2 mmol), trimethylamine (1.4 mmol), and DMAP (cat.) in toluene was heated at 100 C for 72 h. The reaction mixture wasquenched with H20 and extracted with EtOAc. The combined organic layers was dried overNa2SO4 and filtered. Purification via preparative HPLC gave compound 116 in 3% yield. ?HNIVIR(400 1VIHz, DMSO-d6) 11.75 (s, 1H), 11.22 (s, 1H), 7.74 (d, J= 8.1 Hz, 1H), 7.71 -7.64 (m,2H), 7.59 (dd, J= 8.9, 7.1 Hz, 1H), 7.48 -7.36 (m, 2H). ?3C NIVIR (101 MHz, DMSO) 169.04,169.01, 135.08, 135.04, 134.91, 132.60, 127.08, 125.13, 122.59, 111.35.

The synthetic route of 5-Aminoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

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

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. HPLC of Formula: C8H6N2O2

After 80 parts of water was added to 4- (manufactured by Tokyo Kasei Kogyo Co., Ltd.) amino phthalimide 16.2 parts, 0.4 parts of sodium hydroxide was added and dissolved.Under ice cooling, 35% aqueous sodium nitrite solution 19.7 parts was added, followed by 35% hydrochloric acid 26.2 parts was stirred for 2 hours and dissolved by adding little by little to obtain a suspension containing a diazonium salt.[0068]Then, 23.9 parts of 6-amino-4-hydroxy-2-naphthalenesulfonic acid was suspended in 100 parts of water, with sodium hydroxide, the pH was adjusted to 9.0.Here it was added dropwise by a pump over a period of suspension 15 minutes including the diazonium salt.After completion of the addition, to obtain a suspension of yellow by stirring for an additional 30 minutes.After stirring for 1 hour the suspension was stirred for 1 hour.The obtained filtered red solid was dried under reduced pressure at 60 C., to obtain a compound represented by formula (I-1) 40.5 parts.Measurement of the maximum absorption wavelength of this compound, lambdamax was 545nm.

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

Reference:
Patent; Sumitomo Chemical Company Limited; Ashida, Toru; (22 pag.)JP5831135; (2015); B2;,
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, Computed Properties of C8H6N2O2

2.0 parts of a formyl derivative represented by the following formula (2) and 2.0 parts of 4-aminophthalimide represented by the following formula (3) are added to 20 parts of acetic acid and stirred at 40 C. for 6 hours The solution thus obtained was cooled to room temperature, poured into 50 parts of water, stirred for 30 minutes, and the precipitated solid was collected by filtration, washed with water and dried to obtain No. 1 of the above specific example. 1.5 parts of a methine compound (lambda max: 435 nm) represented by 1 was obtained.

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:
Patent; NIPPON KAYAKU COMPANY LIMITED; TAKAHASHI, MASAYUKI; (14 pag.)JP2015/189767; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem