Tag: M.W=100-200

These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, 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. Recommanded Product: 5-Nitroindoline-2,3-dione

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]·2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

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

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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.

Compound 1E (100 mg, 423 mmol), compound 24A (63 mg, 465 mmol) and cesium carbonate (303 mg, 930mmol) were added to NMP (1 mL). The reaction solution was heated to 120 C and stirred for 2 hours, and then thereaction was quenched with water, and extracted with ethyl acetate (3 x 10 ml). The organic layer was washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waschromatographed on a silica gel plate (dichloromethane/methanol = 10: 1, Rf = 0.2) and purified to give compound 24B(yellow solid, 80 mg, 57%).LCMS (ESI) m/z: 336.1(M+1)+

Statistics shows that Indolin-5-ol is playing an increasingly important role. we look forward to future research findings about 172078-33-0.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; LONG, Chaofeng; CHEN, Zhengxia; CHEN, Xiaoxin; ZHANG, Yang; LIU, Zhuowei; LI, Peng; CHEN, Shuhui; LIANG, Guibai; XIE, Cheng; LI, Zhengwei; FU, Zhifei; HU, Guoping; LI, Jian; (276 pag.)EP3293177; (2018); 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 6341-92-0 as follows. Recommanded Product: 6-Chloroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 14192-26-8, 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.

To a yellow solution of methyl 2-oxoindoline-6-carboxylate (6.24 g, 31.7 mmol, Eq: 1) and methyl iodide (9.08 g, 4 ml, 64 mmol, Eq: 2.02) in dry dimethylformamide (90.5 ml) was added portionwise a suspension of NaH in mineral oil (60% w/w, 2.54 g, 63.4 mmol, Eq: 2) over 1.5h while controlling the exothermicity with a water bath. The reaction mixture was carefully poured on an icecooled mixture of -1 1 g sodium hydrogenocarbonate, water (150 mL) and ethyl acetate(150 mL). The resulting mixture was extracted with ethyl acetate and the organic layers were washed with brine. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo.The residue was triturated with heptane ethyl acetate 1:1 and the precipitate was filtered and washed with heptane ethyl acetate 1:1. The solid was dried in vacuo to afford the desired product as a light brown solid (5.026 g, 72%).MS (mlz) = 218.1 [M + H].

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(Chloromethyl)isoindoline-1,3-dione

Benzyl 3-methyl-4-oxo-piperidine-1-carboxylate (20 g, 0.08 mol) was dissolved in THF (300 mL) under N2. The solution was cooled to -78 C and LiHMDS (1M in THF, 101.1 mL, 0.1 mol) was added dropwise over 20 minutes, keeping the temperature below -70 C. After stirring at -78 C for 90 minutes, a solution of 2-(chloromethyl)isoindoline-1,3-dione (23.7 g, 0.12 mol) in THF (200 mL) was added dropwise over 25 minutes, keeping the temperature below -70 C. The reaction was stirred at -78 C for 1 hour then quenched at -78 C by the addition of saturated aqueous ammonium chloride solution (65 mL) and the mixture allowed to warm to ambient temperature. The reaction was repeated and the two mixtures obtained were combined and extracted with EtOAc (300 mL). The organic phase was washed with saturated aqueous sodium bicarbonate solution (300 mL) and brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by chromatography (silica, EtOAc/Petroleum ether elution). Product fractions were combined and concentrated in vacuo and the residue recrystallized from EtOAc to give the product as a white solid (7.56 g, 23 %).

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; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BLEICH, Matthew; CHARRIER, Jean-Damien; DONG, Huijun; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KNEGTEL, Ronald; MOCHALKIN, Igor; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; QIU, Hui; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (312 pag.)WO2019/148136; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 774-47-0,Some common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, molecular formula is C8H3F2NO2, 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: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Difluoroindoline-2,3-dione, its application will become more common.

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. 17630-75-0, name is 5-Chloro-2-oxindole, A new synthetic method of this compound is introduced below., Product Details of 17630-75-0

A 5 mL of ethanol solution containing 5-chlorooxindole (167 mg, 1 mmol), 2- pyridine-carboxaldehyde (129 mg, 1.2 mmol) and 3 drops of piperidine was stirred at 80C for 6 hours. After cooling the solution to 5C, yellow precipitate was obtained (200 mg, 78%). MS: TITLE 257 [M+1] +.

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; IRM LLC; THE SCRIPPS RESEARCH INSTITUTE; WO2004/37247; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20870-79-5, 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 20870-79-5 as follows.

To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2005/256144; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid.

Statistics shows that Potassium 1,3-dioxoisoindolin-2-ide is playing an increasingly important role. we look forward to future research findings about 1074-82-4.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-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.

General procedure: Substituted isatin (10 mmol) was dissolved in hydrazine hydrate (98%, 10 mL, 32.5 mmol) and refluxed for 15-30 min (130 C). The reaction mixture was then poured into cold water, extracted withethyl acetate. The organic layer was then dried over sodium sulfate. Evaporation of the solvent and recrystallization from hexane/ethylacetate provided the substituted oxindole.

Statistics shows that 6-Chloroisatin is playing an increasingly important role. we look forward to future research findings about 6341-92-0.

Reference:
Article; Zhang, Lidan; Ren, Wen; Wang, Xiaoyan; Zhang, Jiaying; Liu, Jie; Zhao, Lifeng; Zhang, Xia; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1071 – 1082;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem