Tag: M.W=100-200

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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

Step 1: Preparation of 4-amino-7-bromoisoindolin-1,3-dione (38) To a solution of 4-aminoisoindolin-1,3-dione (37) (0.5 g, 3.08 mmol) in MeOH (50 mL) was added a mixture of NBS (0.58 g, 3.24 mmol) as three portions at room temperature. Then, the mixture thus obtained was stirred at room temperature for 8 hours, and filtered. The filtrate was concentrated to give the crude product of 4-aminoisoindolin-1,3-dione 38 (0.42 g) as a solid, which was directly used in the next step without further purification.

The synthetic route of 2518-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GREEN CROSS CORPORATION; CHOI, Soongyu; PARK, Eun-Jung; SEO, Hee Jeong; KONG, Younggyu; SON, Ickhwan; MA, Sang-ho; CHA, Man-Young; KIM, Mi-Soon; PARK, Kisoo; (143 pag.)US2016/311772; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, 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 114041-16-6 as follows.

General procedure: Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%)

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 15861-30-0, These common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, 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.

2, 3-Dihydro-1H-indole-5-carboxylic acid (12.4 mmol) was dissolved in DMF (5 mL) and 1, 2-dichloroethane (40 mL). DIPEA (12.4 mmol), 1- (3-dimethylaminopropyl)- 3-ethyl-carbodiimide hydrochloride (12.4 mmol), 1-hydroxybenzotriazole (12.4 mmol) and 2-aminothiazole (12.4 mmol) was added. Stirred at 50 C for 48h. HC1 (2M) (12.4 mmol) was added to the reaction mixture followed by water (30 mL). This gave a heavy precipitation which was removed by filtration. The solid was washed with water and 1,2-dichloroethane and dried. Yield: 56% 1H NMR (D6-DMSO) : 6.60 (s, 1H); 7.26 (d, 1H); 7.44-7. 54 (2H); 7.56 (d, 1H); 7. 86 (d, 1H); 8.45 (s, 1H) ; 11.51 (br s, 1H).

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/39572; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. name: 7-Chloroisatin

General procedure: In sealed tube, a solution of 3 mL solvent (DMSO or DMF) of hydrazines 1 (0.5mmol), diketones 2 or 4 (0.5mmol), K2CO3 (1mmol), eosin Y (0.025mmol) was sequentially added. The reaction mixture was stirred under incandescent light (0.4 Wcm-2) irradiation at 45 °C for 24 h. Then, the mixture extracted with ethyl acetate (3 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 or 5 (PE: EA = 20:1).

The synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diao, Pinhui; Ge, Yanqin; zhang, Wenpei; Xu, Chen; Zhang, Nannan; Guo, Cheng; Tetrahedron Letters; vol. 59; 8; (2018); p. 767 – 770;,
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 32372-82-0 as follows. Application In Synthesis of Isoindoline hydrochloride

l-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.25g, 6.54 mmol, 2.0 eq.) was added to a stirred solution of S6 (1.0 g, 3.27 mmol, 1 eq.), isoindoline hydrochloride (663 mg, 4.26 mmol, 1.3 eq.), 1-hydroxybenzotriazole (1.0 g, 6.54 mmol, 2 eq.) N-,N- diisopropylethylamine (1.72 mL, 9.81 mmol, 3.0 eq.) in dichloromethane (33 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over sodium sulfate, filtered and concentrated. The residue residue was purified by flash chromatography (Si02, 1 :3hexanes/ethylacetate) to afford S7 (1.22 g, 91.8%) as a colorless oil. 1H MR (400 MHz, CDC13) delta 7.50 (s, 1H), 7.37 – 7.26 (m, 3H), 7.19 – 7.12 (m, 2H), 4.99 (s, 2H), 4.82 (s, 2H), 4.68 (s, 2H), 4.62 (s, 2H), 3.88 (s, 3H), 3.48 (s, 3H). HRMS (ESI+) m/z [M + H+] calcd forC11H14BrO5, 452.1072, found 452.1066.

According to the analysis of related databases, 32372-82-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6341-92-0, A common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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.

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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

Related Products of 20870-79-5, 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. 20870-79-5 name is 5-Nitroindolin-2-one, 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.

5-Nitro-1,3-dihydro-indol-2-one (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of 5-amino-1,3-dihydro-indol-2-one as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US6846839; (2005); 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Acetylindolin-3-one

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of Isatin 1a (1 mmol) in water (20 ml)at 60 °C was added o-phenylenediamine 2 (1 mmol). The resulting mixture was stirred and beta-cyclodextrin(15 molpercent) was added to the solution. The reaction progress was monitored using TLC by mixture of Hexane ? EtOAc (6/4). The completion of the reactionas indicated by TLC in UV-chamber and vapour iodine chamber. The reaction mixture was cooled to room temperature and mixture was extracted by ethyl acetate(2 30mL) and dried over anhydrous sodium sulfate.Ethyl acetate removed in vacuum and crude product obtained. To recycle beta-cyclodextrin, acetone was added in the aqueous media, beta-cyclodextrin recovered. Pure product (6H-Indolo[2,3-b]quinoxaline3a) was obtained by silica gel column chromatography(Hexane/EtOAc) = (7/3 ? 6/4) as solid.

The chemical industry reduces the impact on the environment during synthesis 7-Methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shivhare, Km Neha; Siddiqui; Supramolecular Chemistry; vol. 31; 1; (2019); p. 52 – 61;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem