Category: 1504-06-9

1504-06-9, name is 3-Methyloxindole, 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. Recommanded Product: 3-Methyloxindole

A solution of 3-methylindolin-2-one (50.0 g, 340 mmol) in MeCN (500 mL) was charged with NBS (66.0 g, 374 mmol) portionwise over 30 min at -20 . The resulting reaction mixture was stirred for 30 min, then poured into ice (2 L) and extracted with EtOAc (3×1 L) . The combined organic layers were dried (Na2SO4) and concentrated to afford 5-bromo-3-methylindolin-2-one.1H NMR (300 MHz, CDCl3) delta 8.78 (s, 1 H) , 7.36-7.32 (m, 2 H) , 6.79 (d, J 8.7 Hz, 1 H) , 3.51-3.43 (m, 1 H) , 1.49 (d, J 7.8 Hz, 3 H) .

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Application of 1504-06-9, The chemical industry reduces the impact on the environment during synthesis 1504-06-9, name is 3-Methyloxindole, I believe this compound will play a more active role in future production and life.

-Methyloxindole (1.5 g, 10.2 mmol) and lithium chloride (1.26 g, 30 mmol) was dissolved in THF (100 mL). The solution was then cooled to -78 C. and n-butyllithium (4.2 mL, 2.5 M in hexanes, 10.5 mmol) was added slowly over a 15 minute period. Ethyl iodide (4.16 mL, 50 mmol) was added and the mixture was allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate, dried over magnesium sulfate, and concentrated in vacuo. Flash chromatography (SiO2, Hexane/ethylacetate 9/1 then 8/2) gave 3-ethyl-3-methyl-1,3-dihydro-2H-indol-2-one (0.750 g, 25%): HRMS [M+H]+176.1076

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, 3-Methyloxindole, other downstream synthetic routes, hurry up and to see.

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. 1504-06-9, name is 3-Methyloxindole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methyloxindole

General procedure: To a Schlenk tube were added 2-oxindoles 1 (0.3 mmol),Cu(OAc)2 (0.03 mmol), DTBP (0.6 mmol), and 1,4-dioxane (2mL). Then the tube was stirred at 120 C under air for the indicatedtime until complete consumption of starting material asmonitored by TLC analysis. After the reaction was finished, thesolution was concentrated under reduced pressure, and themixture was purified by flash column chromatography oversilica gel (hexane/ethyl acetate) to afford the desired products 2and was analyzed by 1H NMR and 13C NMR spectroscopy andHRMS (see Supporting Information).Typical Data for Representative Compound – 3,3?-Dimethyl-[3,3?-biindoline]-2,2?-dione (2a)d.r. = 19:1, brown solid (0.0701 g, 80% yield). 1H NMR (400 MHz,DMSO-d6): delta = 10.48 (s, 1.9 H), 10.31 (s, 0.1 H), 8.01 (d, J = 3.2Hz, 0.1 H), 7.80 (t, J = 5.1 Hz, 0.1 H), 7.40 (d, J = 1.6 Hz, 0.1 H),7.33 (d, J = 7.6 Hz, 0.1 H), 7.09 (d, J = 7.6 Hz, 1.9 H), 6.96 (t, J = 7.6Hz, 1.9 H), 6.78 (t, J = 7.2 Hz, 1.9 H), 6.54 (d, J = 7.6 Hz, 1.9 H),1.58 (s, 5.7 H), 1.55 (s, 0.3 H).13C NMR (100 MHz, DMSO-d6): delta =179.8, 141.4, 132.3, 128.3, 123.4, 121.5, 109.4, 50.4, 17.6. HRMS(ESI): m/z calcd for C18H17N2O2+ [M + H]+: 293.1285; found:293.1284.

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; Huang, Yi-Ling; Bao, Wen-Hui; Ying, Wei-Wei; Chen, Wei-Ting; Gao, Le-Han; Wang, Xin-Ye; Chen, Gan-Ping; Ge, Guo-Ping; Wei, Wen-Ting; Synlett; vol. 29; 11; (2018); p. 1485 – 1490;,
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

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. 1504-06-9, name is 3-Methyloxindole, A new synthetic method of this compound is introduced below., Product Details of 1504-06-9

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 with EtOAc (*3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120 C.; 1H NMR (DMSO) delta1.32 (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.

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; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1504-06-9, These common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, 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 10 mL Schlenk flask was added 3-methyl 2-indolone (0.2 mmol),Tert-butyl nitrite (t-BuONO, 0.4 mmol) and 1,4-dioxane (2 mL). The reactor was then stirred at 25 C. The reaction progress was monitored by TLC or GC until the reaction mass 3-methyl-2-indolone reaction is complete, The reaction was quenched with saturated brine and the organic phase was recovered. The aqueous phase was extracted with ethyl acetate and the organic phases were combined. The organic phase was dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure.The residue was subjected to column chromatography (n-hexane / ethyl acetate) to give the target product 3-nitro-2-indolinone derivative I-2 in a yield of 71%

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo University; Wu Yi; Wei Wenting; Zhu Wenming; Huang Yiling; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (7 pag.)CN107200705; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, 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 1504-06-9, Recommanded Product: 1504-06-9

General procedure: In an open-air tube at room temperature (25 C), the corresponding 3-substitutedoxindole (0.15 mmol) was added to a solution of organocatalyst 5 (10 mol%) in toluene (1 mL). After 5 minutes, the mixture was introduced into a cooling bath at 0 C, andafter two minutes di-tert-butylazodicarboxilate (0.11 mmol, 1.1 eq.) was added in oneportion. The reaction was then allowed to react for 3 days. After this time, water (5 mL)and ethyl acetate (5 mL) were added, and the aqueous layer was then re-extracted twice (2 x 10 mL). The combined organic phases were dried (MgSO4) and evaporated underreduced pressure. Finally, the reaction crude was purified by column chromatographyon silica gel or TLC preparative using hexane/ethyl acetate mixtures as eluent. Spectroscopic data are listed within the article.

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, 3-Methyloxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Benavent, Lloren; Baeza, Alejandro; Freckleton, Megan; Molecules; vol. 23; 6; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1504-06-9, name is 3-Methyloxindole, 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. SDS of cas: 1504-06-9

A magnetic stirrer was added to the Schlenk tube-sealed reactor, and the 2- oxindole compound of formula II-1 (0.3 mmol) was added, followed by the addition of Cu (OAc) 2 (0.03 mmol) and di-tert-butyl peroxide. (0.6mmol); The reactor was then placed in an oil bath equipped with magnetic stirring, and the reaction was heated and stirred at 120 C for 4 hours. The reaction mixture was completely monitored by TLC. After the completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue was separated by column chromatography (eluent solvent: ethyl acetate / n-hexane) to obtain he title compound formula I-1 , yield 80%.

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (11 pag.)CN108129378; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1504-06-9, name is 3-Methyloxindole, 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 1504-06-9, category: indolines-derivatives

Step 1 : Preparation of 3-methyl-5-(3-trifluoromethylphenyl)- 1 ,3-dihydroindol-2-oneA solution of 3-methyloxindole (5.06 g, 34.4 mmol) in iV,iV-dimethylformamide (60 mL) was cooled to 0 0C. N-Bromosuccinimide (6.23 g, 35.0 mmol) was added, and the resulting solution was stirred for 18 hours while slowly warming to room temperature. The reaction was then diluted with ethyl acetate (100 mL) and washed with 1 :1 saturated aqueous NaCl solutuion:H2O (3 x 75 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid that was used without further purification in the next step described below.A mixture of the crude product described above (1.02 g5 4.51 mmol), 3- (trifluoromethyl)phenylboronic acid (0.983 g, 5.18 mmol), sodium carbonate (0.884 g, 8.34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.252 g, 0.218 mmol) in ethylene glyclol dimethyl ether (8.0 mL) and H2O (1.0 mL) was warmed to 80 0C. After 20 hours, the mixture was cooled to room temperature, poured into 1 : 1 saturated aqueous NaCl solution:H2O (50 mL), and extracted with ethyl acetate (3 x 50 mL). The organic extracts were combined, dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel Biotage 4OM, eluting with 10-35% ethyl acetate/hexanes, to give 3-methyl-5-(3-trifluoromethylphenyl)-l,3-dihydroindol-2-one as a white solid.1H NMR (CDCl3): delta 8.27 (br s, 1 H), 7.79 (s, 1 H), 7.72 (d, I H1 J = 7.3 Hz), 7.56 (m, 2 H), 7.46 (m, 2 H), 6.99 (m, 1 H), 3.55 (dd, 1 H, J = 15.3, 7.8 Hz), 1.57 (d, 3 H, J = 7.7 Hz) MS: m/e 292.41 (M + H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyloxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); 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 1504-06-9 as follows. SDS of cas: 1504-06-9

To a Schlenk reaction flask with a volume of 20 mL, 0.2 mmol of 3-methyl-2-indanone, 0.4 mmol of morpholine, 0.04 mmol of I2, 0.4 mmol of H 2 O 2 and ethanol (2 mL) were added.The reaction flask was stirred at room temperature under an air atmosphere, and the progress of the reaction was monitored by TLC or GC until the reaction of the starting material was complete (8 hours).The reaction mixture after completion of the reaction was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / petroleum ether).

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; Ningbo University; Gao Lehan; Wei Wenting; Bao Wenhui; Xu Xudong; Wang Yining; (10 pag.)CN108440378; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem