Category: 2058-72-2

Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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. 2058-72-2

General procedure: To a stirring mixture of catalyst 1a (0.005 mmol) and cyclohexanone/acetone (5 mmol) in water (500 muL), additive DNP (0.920 mg, 0.005 mmol) was added at 25 C and the mixture was allowed to stir for 5 min followed by addition of isatin derivative (0.5 mmol). The mixture was stirred for 20-96 h and the progress of the reaction was monitored at regular intervals by TLC. On the completion of reaction, saturated solution of NH4Cl (5 mL) was added to it and resulting mixture was extracted with ethyl acetate (3¡Á15 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude aldol product. The column chromatography on silica gel (60-120 mesh) using hexane/ethyl acetate as an eluent gave the corresponding aldol adducts as a syn/anti mixture. The enantiomeric excess of aldol addition products was determined by chiral HPLC. The diastereoselectivity of product was determined by HPLC of crude reaction mixture. Racemic standards were prepared using (¡À) 3-methyl-1-morpholinobutan-2-amine catalyst synthesized form (¡À) valine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-72-2, its application will become more common.

Reference:
Article; Kumar, Akshay; Chimni, Swapandeep Singh; Tetrahedron; vol. 69; 25; (2013); p. 5197 – 5204;,
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 2058-72-2 as follows. 2058-72-2

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: (2E,2’E)-3,3′-Benzene-1,4-diylbis(1-phenylprop-2-en-1-one) (1) (0.34 g, 1 mmol) was added in oneportion at room temperature to a stirred solution of isatinderivative 2 (1 mmol) and L-proline (3) (0.12 g, 1 mmol) inethanol (10 ml). The reaction mixture was stirred for 8 h.The solvent was then removed under reduced pressure, andthe residue was recrystallized from ethyl acetate as white powder.

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; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Keshipour, Sajjad; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 467 – 471; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 467 – 471,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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. 2058-72-2 name is 5-Bromo-1-methylindoline-2,3-dione, 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: To a solution of carboxylic acid (1.3 mmol) in dry CH3CN (3 mL), were added the isatin derivative (1.00 mmol), cyclohexyl isocyanide (1.0 mmol), and sufficiently activated 4 A MS (100 mg). The resultant mixture was stirred at 80 C for the appropriate time as specified in Table 3 and was monitored by TLC. After completion of the reaction, for compounds 4a-o, the solvent was removed under reduced pressure and the residue dissolved in dry CH2Cl2. The 4 A MS was recovered by simple filtration and addition of n-hexane to the filtrate yielded the pure solid products. For compound 4o, the solvent was removed under reduced pressure and the residue was washed with dry CH2Cl2. The solid residue was then dissolved in EtOH, the 4 A MS was recovered by simple filtration, and the filtrate crystallized from ethanol to yield the pure product 4o in 60% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Esmaeili, Abbas Ali; Amini Ghalandarabad, Saeid; Jannati, Saeideh; Tetrahedron Letters; vol. 54; 5; (2013); p. 406 – 408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, A common compound: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A two-necked round-bottom flask with a magnetic stirring bar was flushed with nitrogen at r.t. MgBr2 (225 mg, 1.2 mmol), an N-substituted isatin 1 (1.0 mmol), ethyl propiolate (2; 1.3 equiv) and freshly distilled CH2Cl2 (5.0 mL) were added to the flask. The suspension mixture was stirred at r.t. for 5 h before turning into a pale yellow, homogeneous solution. The reaction was quenched by the dropwise addition of 10 % aqueous NaHCO3 (3 mL). The resulting two phases were separated, and the aqueous phase was extracted with EtOAc (30 mL). The combined organic layer was then washed with brine, dried over anhydrous MgSO4 and concentrated. The obtained crude product was purified by silica gel column chromatography (EtOAc/hexane, 20:80) to afford the corresponding ester 3.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lingam, Kandapalam Arun Prasath; Amutha, Periyasamy; Yuvaraj, Paneerselvam; Selvakumar, Kodirajan; Synthesis; vol. 50; 3; (2018); p. 599 – 606;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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 2058-72-2 as follows.

General procedure: A solution of isatins 1 (0.6 mmol), dienones 2 (0.4 mmol) and proline, thioproline or sarcosine(0.8 mmol) in the 10.0 mL of EtOH at reflux for 3 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc=5:1~3:1) were carried out to furnish the corresponding products 3-5.

According to the analysis of related databases, 5-Bromo-1-methylindoline-2,3-dione, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhou, Gen; Gong, Yi; Wei, Qi-Di; Tian, Min-Yi; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Molecules; vol. 22; 4; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem