Category: 6872-06-6

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. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., SDS of cas: 6872-06-6

General procedure: 2-Methylindoline (400 mg, 3.0 mmol, 1.0 equiv) was dissolved in dry pyridine (10 mL). Methane sulfonyl chloride (480 mg, 4.2 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 634 mg, 100 % yield.

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.

Synthetic Route of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

26.6 mg (0.2 mmol) of 2-methylindoline,81.2 mg of ethyl bromodifluoroacetate (0.4 mmol),2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent.The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated.The solvent was removed and the residue was chromatographed on silica gel.It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1.The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined.The solvent was distilled off by a rotary evaporator. Vacuum drying to give a yellow liquid 2-methylindoline-1-carbaldehyde19.7 mg, yield 61%.

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

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
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 6872-06-6 as follows. Application In Synthesis of 2-Methylindoline

(1) 1.19 g of 2-methylindoline and 2.57 g of 2-bromo-4-methylpyridine were added to a 50 mL round bottom flask in a ratio of the amount of the substance: 1:1.5; (2) Stir directly in the air and mix evenly at room temperature.Then heated to 100 C, after 26 min the system solidified, stopped the reaction, cooled to room temperature; (3) Add 50 mL of saturated NaHCO3 solution to the system to dissolve the solid.Further, 50 mL of ethyl acetate solution was added, shaken, and liquid-separated, and the aqueous phase was extracted three times with ethyl acetate, 30 mL each time, and the organic phase was combined and concentrated by a rotary evaporator; (4) The concentrated solution was dissolved in 15 mL of ethanol, refluxed at 80 C for 10 min, cooled, and a pale yellow solid was precipitated, filtered, rinsed with water and dried under vacuum to give the desired product.The purity was 97% (NMR analysis) and the yield was 75%.

According to the analysis of related databases, 6872-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Northwest University; Jiao Linyu; Zhang Ze; Yin Xiaomei; Hong Qian; Ning Zihui; Ma Xiaoxun; Li Zhuo; Sun Ming; (11 pag.)CN109265439; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The synthesis of 2-(6-(indolin-1 -yl)-6-oxohexyl)phthalimide 5.2.4 was performed following the report of Krasnov and co-workers ( see Krasnov et al., Mendeleev Commun. 25:412 (2015)): To a stirred solution of aniline (1 .0 equiv) and A/,A/-diethylaniline (1 .0 equiv) in 0.2 M dry CH2CI2was added a 0.2 M solution of acid chloride (1 .0 equiv) in dry CH2CI2dropwise over 10 min. After stirring at room temperature for 16 h, a 1 .0 N aq soln of HCI was added to the reaction mixture. After 30 min, the reactives were diluted with 20 ml. of EtOAc and washed with 2 c 20 ml. of water and 20 ml. of a 5% aq soln of NaHC03. The resulting organic phase was dried over Na2S04, filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by MPLC to afford the product.

The chemical industry reduces the impact on the environment during synthesis 2-Methylindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE BOARO OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; THE TRUSTEES OF INDIANA UNIVERSITY; DRIVER, Tom, G.; MACHADO, Roberto, F.; SU, Naijing; GUAN, Xinyu; MAZUMDAR, Wrickban; RATIA, Kira; HICKOK, Jason, Ralph; LOCKETT, Angelia, Denise; (159 pag.)WO2019/153007; (2019); A2;,
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. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., Computed Properties of C9H11N

Example 1Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(methylsulfonyl)indolineReagents MW Mole Reagent/raw material (g/mole) Quantity moles ratio 2-methylindoline 161.20 1 g 7.5 mmol 1 eq. methanesulfonyl chloride 114.55 1.04 g 9.0 mmol 1.5 eq. 2-methyl-1-(methyl- 239.29 276 mg 1.3 mmol 1.2 eq. sulfonyl)indoline 2,3-dihydro- 375.93 250 mg 1.06 mmol 1.0 eq. benzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 170 mg 1.3 mmol 1.2 eq. Step I: 2-methylindoline was dissolved in 5 mL dry pyridine, and methanesulfonyl chloride was dropped in 2 portions under N2. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When the reaction was complete as determined by HPLC (product Rt=8.51 min, st. material Rt=4.18 min) using the H2O-Acetonitrile (CAN) gradient given below with a Gemini-NS C18, 3 mum, 100 , 150¡Á4.6 mm column chromatography as well as by TLC (8/2 PE/EtOAC), the crude reaction was poured into 100 mL cold 0.5M HCl, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated, and the evaporation residue was purified by passing through a silica plug (100 g silica gel in large sinter glass). The product eluted in 7/3 PE/EtOAC, while all of the pink polar byproduct was retained on silica. The organic phase was dried on Na2SO4, and then evaporated and used for the next step without further purification (Product 100% pure, 455 mg, yield 30%).HPLC Purification Protocol Time (min) FlowH2O (%) ACN (%) 1 100 0 0.02 1 100 0 11.0 1 0 100 13.0 1 100 0 18.0 1 100 0 18.1 0.2 100 0

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6872-06-6, The chemical industry reduces the impact on the environment during synthesis 6872-06-6, name is 2-Methylindoline, I believe this compound will play a more active role in future production and life.

General procedure: 2-Methylindoline (400 mg, 3.0 mmol, 1.0 equiv) was dissolved in dry pyridine (10 mL). Methane sulfonyl chloride (480 mg, 4.2 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 634 mg, 100 % yield.

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, 2-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Sherman, Daniel; Aizikovich, Alex; Shitrit, Alina; Ben-Zeev, Efrat; Schutz, Nili; Bohana-Kashtan, Osnat; Konson, Alexander; Behar, Vered; Becker, Oren M.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 20; (2012); p. 6460 – 6468;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6872-06-6,Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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.

Pd(OAc)2 (1.12 mg, 0.005 mmol), Zn(OTf)2 (3.63 mg, 0.01 mmol) were dissolved in 5 mL acetonitrile in a glass tube, after stirring for 10 min, indoline (60 mg, 0.5 mmol) were added. The glass tube was equipped with a reflux condenser. Next, the reaction solution was magnetically stirred at 353K in oil bath for 6 h with O2 balloon. The product analysis was performed by GC using the internal standard method. Control experiments including using Pd(OAc)2, or Zn(OTf)2 alone were carried out in parallel.

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

Reference:
Article; Lou, Chenlin; Qin, Shuhao; Zhang, Sicheng; Lv, Zhanao; Senan, Ahmed M.; Chen, Zhuqi; Yin, Guochuan; Catalysis Communications; vol. 90; (2017); p. 5 – 9;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem