Tag: M.W=100-200

17564-64-6, name is 2-(Chloromethyl)isoindoline-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. Application In Synthesis of 2-(Chloromethyl)isoindoline-1,3-dione

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.60 2-((2-(2-(Heptan-3-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (8C) White powder, mp 70-74 C, 86% yield; 1H NMR (400 MHz, CDCl3): delta 0.82-0.93 (m, 2H, CH2, 3H, CH3), 1.08-1.12 (m, 1H, CH2), 1.30-1.37 (m, 3H, CH3), 1.51-1.55 (m, 1H, CH2), 2.24-2.32 (m, 2H, CH2), 2.36-2.44 (m, 2H, CH2), 3.82 (s, 2H, CH2, thiazolidinone), 5.71 (s, 2H, ArCH2), 7.73-75 (m, 2H, Ar), 7.85-7.86 (m, 2H, Ar).

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 110568-64-4, The chemical industry reduces the impact on the environment during synthesis 110568-64-4, name is 6-Nitroisoindolin-1-one, I believe this compound will play a more active role in future production and life.

Step d:[00296] A mixture of 5-nitro-2,3-dihydro-isoindol-l-one derivative (l eq), 10% Pd-C (0.05 eq) and 10 mL AcOEt is hydrogenated at room temperature for 6hrs. The catalyst is removed by filtration through Celite and the filtrate is evaporated to afford the title compound.

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, 6-Nitroisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; BLANC, Javier; HODGES, Alastair, James; BURLI, Roland, Werner; BRECCIA, Perla; BLACKABY, Wesley, Peter; VAN ROMPAEY, Luc, Juliaan, Corina; FLETCHER, Stephen, Robert; WO2010/10184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 317-20-4, 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. 317-20-4 name is 7-Fluoroisatin, 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.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

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

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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., Recommanded Product: 7-Chloroisatin

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol percent) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1?41.

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:
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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. 366453-22-7, name is 4-Methoxyisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Methoxyisoindolin-1-one

Step c: To an ice-cold solution of [11C] (291 mg, 1.78 [MMOL)] in CH2CI2 (20 mL) was added a 1.0 M BBr3 solution in [CH2CI2] (3.6 mL, 3.6 [MMOL).] The cold bath was then removed and the resulting solution was stirred for 16 h at ambient temperature. The reaction was carefully quenched by the addition of water and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried [(MGS04),] filtered and evaporated to dryness to give [11D] (232 mg, 87% yield) as beige solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 366453-22-7.

Reference:
Patent; BOEHRINGER INGELHEIM (CANADA) LTD.; WO2004/26875; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 25369-33-9, 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.

General procedure: Appropriate indolin-2-one or indoline-2-thione (0.3 g) was mixed with acetic anhydride (3 mL) and 4-dimethylaminopyridine (DMAP, 1 mol %). The mixture was heated at 150 C in a round-bottomed flask equipped with an air condenser and CaCl2 guard tube. The reaction time for each reactant is provided in [Table 2] and [Table 3]. After the completion of the reaction excess acetic anhydride was evaporated under reduced pressure. The solid residue obtained in the case of the triacetylated products was suspended in cold methanol and vacuum filtered. The product collected was thoroughly washed with hexane and dried. In the case of mono and diacetylated products the solid residue was purified using flash column chromatography (FCC) (silica gel, hexanes/ethyl acetate).

The synthetic route of 25369-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 19155-24-9, 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. 19155-24-9, name is 3,3-Dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3,3-dimethylindolin-2-one (31) (12.9 mg, 0.08 mmol), 4-bromo-2-methoxybenzonitrile (30) (17.0 mg, 0.08 mmol), COPPER (I) IODIDE (7.80 mg, 0.04 mmol), TRANS- (1R, 2R)- N, N’- DIMETHYL- CYCLOHEXANE- 1, 2- DIAMINE (11.7 mg, 0.08 mmol) and POTASSIUM PHOSPHATE (35.0 mg, 0.16 mmol) in DMSO (0.50 mL) was heated to 80C for 1.5 h, then heated to 100C for 21h. The reaction mixture was diluted with ethyl acetate, filtered through a plug of silica gel and concentrated by rotary evaporation. The resulting residue was purified by prep-HPLC to afford 4-(3,3-dimethyl-2-oxoindolin-1-yl)-2-methoxybenzonitrile (32) (8.75 mg, 37percent). 1H NMR (500 MHz, DMSO-d6) d ppm 1.41 (s, 6 H) 3.95 (s, 3 H) 6.95 (d, J=7.81 Hz, 1 H) 7.14 (t, J=7.32 Hz, 1 H) 7.20 (d, J=7.81 Hz, 1 H) 7.24 (t, J=7.81 Hz, 1 H) 7.36 (s, 1 H) 7.46 (d, J=6.83 Hz, 1 H) 7.90 (d, J=7.81 Hz, 1 H)

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

Reference:
Article; Guo, Chuangxing; Pairish, Mason; Linton, Angelica; Kephart, Susan; Ornelas, Martha; Nagata, Asako; Burke, Benjamin; Dong, Liming; Engebretsen, Jon; Fanjul, Andrea N.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2572 – 2578;,
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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Methylindolin-2-one

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3484-35-3.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1504-06-9,Some common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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.

In the Schlenk bottle to point pen 1 b indicated by the 2 – indolone derivatives (29.4 mg, 0.2 mmol), butyl alcohol peroxide (t – BuOOH, 43.2 mg, 0 . 48 mmol), then adding the solvent water (2 ml), then the reactor in air atmosphere, 80 C stirring under the conditions of the reaction, TLC monitoring the reaction by the disappearance of the process until the raw material (the reaction time is 24 hours), after the reaction, the reaction solution is extracted with ethyl acetate three times, the organic phase dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, the residue by column chromatography (elution solvent: ethyl acetate/hexane) to obtain the target product I – 2. (86% Yield);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyloxindole, its application will become more common.

Reference:
Patent; Ningbo University; Song Sizhe; Wei Wenting; Bao Wenhui; Meng Yanan; Meng Xiaoxiao; (10 pag.)CN109776387; (2019); A;,
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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95percent, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol percent) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem