Tag: M.W=100-200

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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.997 g, 24.9 mmol) in diethyl ether (100 mL) was added dimethyl 2- isobutylmalonate (3.13 g, 16.6 mmol) dropwise. The resulting mixture was stirred at RT for 3 h. The reaction mixture was cooled to 0 C. N-chloromethyl phthalimide (3.24 g, 16.6 mmol) was added in one portion. The reaction mixture was stirred at RT overnight followed by heating to reflux for 1 h. The reaction mixture was cooled to RT and cold 1.5 N HC1 (100 mL) was added. The organic layer was separated. The aqueous layer was extracted with diethyl ether (2 x 50 mL). The combined ether layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (5.3 g, 15.2 mmol, 92 % yield). The crude product was taken to next step without further purification. LCMS (ESI) m/e 347.9 [(M+H)+, calcd for Ci8H22N06, 348.1]; LC/MS retention time (method C): tR = 1.95 min.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Indoline – Wikipedia,
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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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 64483-69-8

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
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Electric Literature of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

The synthetic route of 6-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
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Synthetic Route of 3485-84-5, 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 3485-84-5 as follows.

A mixture of 4-chlorobenzaldehyde tosyl hydrazone sodium salt (1.67g, 5.05mmol), benzyltriethylammoniumchloride (1 15mg, O.deltammol), rhodium acetate (20mg, 0.05mmol) and N-vinylphtalimide (4.32g, 25.0mmol) in dry 1 ,4-dioxane (13ml) was stirred for one day under nitrogen at room temperature. Water (35ml) was added to the mixture and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4. Evaporation gave the crude material, which was purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1 :1 ). To afford 392mg (26.3% of theory) of 2-[2-(4-chloro-phenyl)-cyclopropyl]-isoindole-1 ,3-dione in the form of a solid. 1H NMR (400MHz1 CDCI3): delta 7.73-7.62(m,4H), 7.04-7.01 (m,4H), 3.08(td,1 H,CHN), 2.50(q,1 H1CHPh), 2.19(ddd,1 H,CHH), 1.63(q,1 H1CHH). MS [M+H]+ 298/300.

According to the analysis of related databases, 3485-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED,; WO2007/134799; (2007); 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 14192-26-8

Methyl 2-oxindoline-6-carboxylate (20 g, 105 mmol) was charged to the reaction vessel. The vessel was equipped with thermometer, stirrer and condenser. Toluene (100 ml, 5 vol) was added followed by acetic anhydride (90 ml, 954 mmol) and the mixture was heated to reflux (115-118 C ). Reflux was continued for 18 hours and a sample was analyzed by HPLC for methyl 2-oxindoline-6-carboxylate (nmt 2.0 a-%). When the methyl 2-oxindoline-6-carboxylate was consumed 40 ml (2 vol) of solvent was distilled off followed by addition of fresh toluene (40 ml, 2 vol). Trimethyl orthobenzoate (53.9 ml, 314 mmol) was added to the boiling reaction during a couple of minutes maintaining the temperature above 110 C . After the addition was complete distillation began and the temperature of the reaction mixture was above 120 C. Eight volumes (160 ml) of solvents were distilled of after which the reaction temperature was adjusted between 110-115 C. The reflux was continued for two hours and precipitation of methyl (E)-l -acetyl-3 -(methoxy(phenyl)methylene)-2- oxoindoline-6-carboxylate began during the reaction. According to HPLC- chromatogram 93.6 % conversion was achieved. The reaction mixture was allowed to cool to room temperature during 5 hours, and then further cooled to 0 C and stirred for two hours at 0 C. The precipitate was filtered and washed with EtOAc (2 x 20 ml, 2 x 1 vol) and dried in vacuum oven at 60 C for 16 hours to obtain the product (33.99 g, 90.85 %, 98.36 a-%) as tan powder

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERMION OY; PIISOLA, Antti; TOIS, Jan; (13 pag.)WO2019/97112; (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 71294-03-6 as follows. Safety of 7-Fluoroindolin-2-one

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

According to the analysis of related databases, 71294-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2913-97-5,Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

Intermediate B3-2-(1,3-dioxoisoindolin-2-yl)acetaldehyde oxime A mixture of intermediate B2 (1.46g, 1equiv), hydroxylamine hydrochloride (0.64g, 1.2equiv), anhydrous K2CO3 (1.6g, 1.5equiv) in absolute methanol (10ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water, extracted with dichloromethane three times. The organic phase was combined and washed with brine, dried and solvent evaporated to give the title compound as a white solid (0.75g). 1H-NMR (d6-DMSO, 400 MHz, ca 1:1 cis-trans isomer) delta4.30/4.37 (2x d, 2H, J=4.0), 6.81/7.35 (2x t, 1H, J=4.0), 7.81-7.88 (m, 4H), 10.86/11.34 (2x s, 1H); MS (EI) m/z: 204 (M+).

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; WANG, Kai; EP2725024; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7477-63-6, 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. 7477-63-6 name is 7-Chloroisatin, 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.

0.4 mmol of 7-chloroisonin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under heating at 80 ° C for 48 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-11 (white solid, yield 77percent, purity 99.8percent) was obtained.

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; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4, Recommanded Product: 1-Methylisatin

General procedure: To a mixture of isatin (1 equiv.) and indole (1 or 2 equiv.) in water (3 mL), CuWO4 (10 mol%) was added and the mixture was stirred at room temperature for 2 h or heated at 60 C for 2 h. After completion of the reaction (monitoring by TLC), the mixture was cooled (in the case of bis-indolyl-2-oxindoles) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the desired product which was purified by silica gel column chromatography. Elution of the column with PE:EtOAc gave the desired products (5 or 6).

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:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
Indoline – Wikipedia,
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Application of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture containing isatin derivatives (1 mmol),malononitrile or ethyl cynocette (1mmol) and 1,3-cyclldiketone (1 mmol) in water (5 mL), H-Fe3O4(at)DA-SO3H(0.01g) were added and stirred under reflux condition. The progress of the reaction was monitored by TLC (n-hexane:EtOAc 7:3). After completion of the reaction the mixture was cooled and the catalyst was separated by means of an external magnet from mixture, then the crude product was collected and washed with distilled water and dried. They were weighted for reporting of the yields.

The synthetic route of 5-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirhosseyni, Marzie Sadat; Nemati, Firouzeh; Elhampour, Ali; Combinatorial Chemistry and High Throughput Screening; vol. 21; 7; (2018); p. 487 – 494;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem