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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Safety of 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 611-09-6 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 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1; Preparation of (2-methyl-l,3-dioxo-2,3-dihydro-lH-isoindol-4-yl)acetic acid; Step 1 : 4-Amino-l,3-isoindolinedione; A solution of 3-nitrophthalimide in ethylacetate was treated with 10% palladium on charcoal (10 wt. %) and hydrogenated at 20 psi for 2h. The catalyst was filtered through celite and the filterate was evaporated to give the crude product (97%) which was used without purification in the next step. 1H-NMR (delta ppm, DMSO-J6, 300 MHz): 10.85 (br. s, IH); 7.39 (t, J = 7.8, IH); 6.93 (d, J = 8.4, IH); 6.88 (d, J = 6.9); 6.38 (br. s, 2H).

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

Reference:
Patent; GLENMARK PHARMACEUTICALS, S. A.; WO2009/118596; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7699-18-5, The chemical industry reduces the impact on the environment during synthesis 7699-18-5, name is 5-Methoxyindolin-2-one, I believe this compound will play a more active role in future production and life.

PREPARATION A N-methyl-5-methoxyoxindole 5-methoxy oxindole (450 mg, 2.76 mmol) and potassium carbonate (585 mg, 4.23 mmol) were combined in 45 ml of acetone under an inert atmosphere. To this white, heterogenous mixture was added 0.33 ml of methyl iodide (5.30 mmol) via syringe. The reaction mixture was stirred at room temperature for 10 hours and then at 75 C. for 3 hours. Additional potassium carbonate and methyl iodide were added (290 mg and 0.11 ml, respectively), and the reaction mixture was stirred at 75 C. for 6 more hours. The reaction mixture was then poured into 300 ml of saturated brine solution and extracted with 3*200 ml ether. The combined organic layers were dried over MgSO4, filtered, and stripped to a yellow oil. This was purified via flash chromatography (3:1 ethyl ether/hexane) to provide the title compound (307 mg, 63% yield) as white crystals: m.p. 93-94 C. M/z calculated for C10 H11 NO2: 177.0790, Found: 177.08066.

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, 5-Methoxyindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US5502072; (1996); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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 496-12-8 as follows.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dirnethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1 H, s), 10.32 (1H, s), 7.36 (1H, br.s), 7.35 (1 H1 s), 7.28 (3H, br.s), 6.59 (1H1 s), 4.77 (2H1 br.s), 4.71 (2H1 br.s). MS: [M+H]+ 332/334.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6872-06-6, 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. 6872-06-6 name is 2-Methylindoline, 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.

Under the protection of anhydrous oxygen-free and inert gas, 0.01161 g (1.14¡Á10-5 mol) {L1La[N(SiMe3)2]}2 was added to the reaction flask, and then 148 muL (1.14¡Á10-3 mol) 2- Methyl porphyrin was added to 1.41 mL of tetrahydrofuran and stirred at room temperature for 0.5 hour. Further, 0.34 mL (3.40 x 10-3 mol) of benzaldehyde was added, and after the reaction was stirred for 3 hours, the reaction was completed.Pour the reaction solution into an eggplant-shaped bottle, add a small amount of ethyl acetate to the reaction flask and wash it three times, still pour into the eggplant-shaped bottle.Add appropriate amount of silica gel, spin dry, and then load on the packed column of silica gel.The column was passed through a suitable eluent (ethyl acetate: petroleum ether = 1: 6) to afford product, yield 75%.

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

Reference:
Patent; Soochow University (Suzhou); Zhao Bei; Xiao Yang; Lu Chengrong; (18 pag.)CN104817583; (2019); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-1,3-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 7147-90-2, SDS of cas: 7147-90-2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added benzylmagnesium chloride (2 M in THF, 30 mL) dropwise at 0 C. After the addition, the reaction mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regio isomers (5.47 g, 100%). MS: 274.1 (M+H+).; Under N2 protection, triethylsilane (23 g, 200 mmol) and TFA (10 mL) were added successively to a mixture of 3-benzyl-5-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one and 3-benzyl-6-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one (5.47 g, 20 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. NaHC03 solution (30 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 3-benzyl-5-chloro-2,3-dihydro-isoindol- 1 -one was obtained by prep- HPLC separation as a white solid (1.03 g, 20%). MS: 258.1 (M+H+).

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 550-44-7, Name is 2-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2. In an article, author is Yang, Ping,once mentioned of 550-44-7, Formula: C9H7NO2.

Pd-Catalyzed Dearomatization of Indole Derivatives via Intermolecular Heck Reactions

The Summary of main observation and conclusion Pd-catalyzed intermolecular dearomative Heck reaction of indoles with aryl iodides is described. The challenges on both reactivity and regioselectivity are addressed by the judicious regulation of the geometric and electronic properties of the substrates. An array of indoline derivatives bearing C2-quaternary center is obtained in good to excellent yields (up to 93%) with exclusive regioselectivity under operationally simple conditions. The mechanistic proposal is supported by detailed DFT calculations.

Interested yet? Keep reading other articles of 550-44-7, you can contact me at any time and look forward to more communication. Formula: C9H7NO2.

Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology. 59-48-3, Name is Indolin-2-one, molecular formula is , belongs to indolines-derivatives compound. In a document, author is Filatov, Vadim, Computed Properties of C8H7NO.

Synthesis of 1,3-diaryl-spiro[azetidine-2,3 ‘-indoline]-2 ‘,4-diones via the Staudinger reaction: cis- or trans-diastereoselectivity with different addition modes

A new synthetic approach for realizing biologically relevant bis-aryl spiro[azetidine-2,3 ‘-indoline]-2 ‘,4-diones was developed based on Staudinger ketene-imine cycloaddition through the one-pot reaction of substituted acetic acids and Schiff bases in the presence of oxalyl chloride and an organic base. A series of [azetidine-2,3 ‘-indoline]-2 ‘,4-diones were synthesized using this method. For comparison, the same compounds were obtained using a known technique, where ketene is generated from pre-synthesized acyl chloride. It was shown that the use of oxalyl chloride for ketene generation in the one-pot reaction at room temperature allows for the reversal of the diastereoselectivity of spiro-lactam formation, unlike previously described procedures.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 59-48-3, in my other articles. Computed Properties of C8H7NO.

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, such as the rate of change in the concentration of reactants or products with time. 56341-37-8, Name is 6-Chlorooxindole, formurla is C8H6ClNO. In a document, author is Zhou, Hai-Shan, introducing its new discovery. Quality Control of 6-Chlorooxindole.

Design, Synthesis, and Structure-Activity Relationships of Indoline-Based Kelch-like ECH-Associated Protein 1-Nuclear Factor (Erythroid-Derived 2)-Like 2 (Keap1-Nrf2) Protein-Protein Interaction Inhibitors

The Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor erythroid 2-related factor 2)-ARE (antioxidant response element) pathway is the major defending mechanism against oxidative stresses, and directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has been an attractive strategy to target oxidative stress-related diseases, including cardiovascular diseases. Here, we describe the design, synthesis, and structure-activity relationships (SARs) of indoline-based compounds as potent Keap1-Nrf2 PPI inhibitors. Comprehensive SAR analysis and thermodynamics-guided optimization identified 19a as the most potent inhibitor in this series, with an IC50 of 22 nM in a competitive fluorescence polarization assay. Further evaluation indicated the proper drug-like properties of 19a. Compound 19a dose-dependently upregulated genes and protein level of Nrf2 as well as its downstream markers and showed protective effects against lipopolysaccharide-induced injury in both H9c2 cardiac cells and mouse models. Collectively, we reported here a novel indoline-based Keap1-Nrf2 PPI inhibitor as a potential cardioprotective agent.

If you are hungry for even more, make sure to check my other article about 56341-37-8, Quality Control of 6-Chlorooxindole.

Catalysts are substances that increase the reaction rate of a chemical reaction without being consumed in the process. 56341-37-8, Name is 6-Chlorooxindole, SMILES is O=C1NC2=C(C=CC(Cl)=C2)C1, belongs to indolines-derivatives compound. In a document, author is Reddy, Angula Chandra Shekar, introduce the new discover, Safety of 6-Chlorooxindole.

Diastereoselective Palladium Catalyzed Carbenylative Amination of ortho-Vinylanilines with 3-Diazoindolin-2-ones

A diastereoselective palladium catalyzed carbenylative amination of ortho-vinylaniline with 3-diazoindolines-2-one have been accomplished for the synthesis of various tetrasubstituted indoline fused spirooxindole with good yields and diastereoselectivity. Notable features of the method include construction of two contiguous tetrasubstituted carbon stereocenters via C-N and C-C bond formation in single operation, wide functional group tolerance and high atom and step economy. Importantly, the present reaction was also extended to one-pot conversion of tosylhydrazones and ortho-vinylanilines to spirooxindole derivatives.

The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 56341-37-8 is helpful to your research. Safety of 6-Chlorooxindole.