Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, Computed Properties of C8H4ClNO2

5mmol of o-phenylenediamine in turn,5mmol 7-chlorodione indole,6mmol iodoethane,1mmol p-toluenesulfonic acid,1mmol selective fluorine reagent,20ml of toluene was added to the round bottom flask,Stir at reflux at 70-90 C for 24 hours. After the reaction is complete, add 30 ml of brine to quench the reaction. The reaction mixture is extracted with 90 ml of ethyl acetate three times to extract the reaction product. An analytically pure 7-chloro-6-ethyl-6H-indole [2,3-b] quinoxaline was obtained. Red solid, 81% yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Chloroisatin, and friends who are interested can also refer to it.

Reference:
Patent; South China Normal University; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Song Xinlong; Zhou Guofu; Pan Junyou; (10 pag.)CN110283177; (2019); 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 1504-06-9 as follows. COA of Formula: C9H9NO

5-bromo-3-methyl-indol-2-one Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3). was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted EtOAc (*3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120 C.; 1H NMR (DMSO) delta 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm-1; MS (EI) m/z 224/226 (M-H)-; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 25369-33-9, name is 7-Chloroindolin-2-one, 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. Safety of 7-Chloroindolin-2-one

General procedure: A mixture of 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

The synthetic route of 7-Chloroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Chloroisatin

The specific steps are:Add 7-chloroindole (54.5 mg, 0.3 mmol) to the pressure tube.Benzamidine hydrochloride (140.9 mg, 0.9 mmol),CuI (5.7 mg, 0.03 mmol)And potassium phosphate (381.6 mg, 1.8 mmol).Add 3mL of DMSO,After magnetic stirring at room temperature for 5 hours,The reaction solution was extracted with dichloromethane.The organic layer was washed with saturated brine.After drying anhydrous sodium sulfate,The solvent is distilled off under reduced pressure to obtain a crude product.The crude product is purified by column chromatography with dichloromethane/petroleum ether=1:20 (V/V) as the eluent to obtain the desired product. The product is a yellow solid.The yield was 68percent.

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; Wuhan Institute of Technology; Jia Fengcheng; Chen Yunfeng; (8 pag.)CN108558782; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 340702-10-5, A common heterocyclic compound, 340702-10-5, name is 6-Fluoroisoindolin-1-one, molecular formula is C8H6FNO, 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 6-fluoroisoindolin-1-one (10 g, 66.2 mmol) in anhydrous dichloromethane (100 mL) were added triethylamine (16.72, 165.5 mmol, 21.8 mL), (Boc)2O (17.3 g, 79.4 mmol) and catalytic DMAP (100 mg) at room temperature. The reaction mixture was stirred at room temperature for 16 h. After completion, the reaction mixture was diluted with CH2Cl2, washed with H2O, and then saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude compound was purified by silica gel chromatography (0-30% ethyl acetate in hexanes) to give the product. MS: (ES) m/z calculated for C13H14FNO3 [M+H]+ 252.3, found 252.3.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 611-09-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 611-09-6, its application will become more common.

Reference:
Article; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52351-75-4, name is 6-Methoxyindoline-2,3-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 52351-75-4, Application In Synthesis of 6-Methoxyindoline-2,3-dione

Step 3: Preparation of 7-methoxy-2-phenyl-quinoline-4-carboxylic acid 112.Compound 111 (500 mg, 1 eq.) and acetophenone (380 muL, 1.2 eq.) were added at room temperature to a solution of KOH (520 mg, 3.3 eq.) in ethanol (5 mL). The reaction mixture was stirred at 70 0C for 7 hrs. The mixture was then poured into ice/water, and washed with dichloromethane. Aqueous layer was acidified with 3N HCl to pH 2-3. The precipitate obtained was filtered, washed with water, and triturated in ethanol to yield compound 112 as a beige solid in 40% yield. MS (ESI, EI+): m/z = 280 (MH+).

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; IDENIX PHARMACEUTICALS, INC.; WO2009/14730; (2009); 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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6FNO2

Step 2: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one 7-Fluoro-1-methyl-1H-indole-2,3-dione (Step 1, 1.05 g, 5.86 mmol) is heated with neat hydrazine hydrate (10 ml) at 130 C. for 1 hour. The mixture is cooled, diluted with ice water and extracted with ethyl acetate. The extract is washed with brine, dried (Na2SO4), and evaporated to give the title compound as a light yellow solid. HPLC r.t. 4.07 min; MS for C9H8FNO m/z 165.16 (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:
Patent; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

N-(2-hydroxyethyl) phthalimide (100 g, 0.52 M) was coupled with 4-chloroethyl acetoacetate (50 g, 0.30 M) in the presence of sodium hydride in toluene under nitrogen atmosphere at ?11 to ?15 C. and at 25-30 C. for 12 hours and at 45 C. for 1 hour. The reaction mass was quenched in acidic water and extracted with toluene. The toluene extract was subjected to distillation and residue was degassed below 60 C.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Hydroxyethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Purohit, Arun Kumar; Desai, Brahmader Chilu; Shete, Balasaheb Dashrath; Bagwan, Salim Abbas; US2004/44218; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

19155-24-9, name is 3,3-Dimethylindolin-2-one, 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. Formula: C10H11NO

General procedure: To a solution of c1 ? c2 (1.0 equiv) and PIFA (1.2 equiv) in CH2Cl2 was stirred for 30 minutes at room temperature, then trifluoroacetate (10.0 equiv) was added to the mixture which was further stirred for 24 h at room temperature. Then, the reaction mixture was neutralized by sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases were dried and concentrated in vacuum and the residue was purified by silica gel chromatography (petroleum ether/ ethyl acetate = 1:1) to give d1 ? d2 (yield 50percent ? 60percent) as yellow solid.

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Kai; Li, Shiyu; Lv, Xiao; Tian, Yongbin; Kong, Haiyan; Huang, Xufeng; Duan, Yajun; Han, Jihong; Xie, Zhouling; Liao, Chenzhong; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 1012 – 1018;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem