Month: May 2021

Electric Literature of 15861-30-0,Some common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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.

A 50 ml. RBF was charged with indoline-5-carboxylic acid (2 g, 12.3 mmol), methanol (25 ml_, 0.5 M) and H2S04 (1 mlcat.). The reaction mixture was stirred at reflux for 8 h. The methanol was concentrated under reduced pressure and the resulting residue was extracted with dichloromethane (2 x 25 ml.) and the combined organic layer was washed with sat. NaHC03 (1 x 20 ml_). The combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford methyl, indoline- 5-carboxylate (2.1 g , 2.78 g theoretical, 75.5%). The product was used directly in the next step without further purification.

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLLABORATIVE MEDICINAL DEVELOPMENT PTY. LTD.; WARNER, John, C.; BALDINO, Carmen; MUOLLO, Lauren; ROSENFELD, Craig; (109 pag.)WO2019/106434; (2019); 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. 18711-15-4, name is 4,6-Dichloroisatin, A new synthetic method of this compound is introduced below., name: 4,6-Dichloroisatin

Accurately weighed 4,6-dichloro isatin (0.56 g),Sarcosine (0.25 g)Was added to a 100 mL flask,Add about 50mL ethanol solvent,Dropwise pulegone (0.3 g).The reaction was carried out under conditions catalyzed by phosphotungstic acid (0.5 g), heated to 80 C with a heat jacket,Placed on a magnetic stirrer,Reflux reaction for 6 hours,The reaction solution was concentrated by rotary steam and then filtered,The obtained filter cake was recrystallized by adding 50 ml of a mixed solution of ethyl acetate and petroleum ether 1: 1,A pale yellow crystalline powder (0.57 g)The overall yield was 72.6%.

The synthetic route of 18711-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi University of Science and Technology; Liang, Chengyuan; Song, Huihui; Chang, Xiangna; (15 pag.)CN104193749; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

1 mole of Piperazine Benzisothiazole hydrochloride, 1 mole of 5-(2-chloroethyl)- 6-chlorooxindole, 3.3 mole of Sodium carbonate, water 5.2 times based on oxindole weight and 1 % of dispersing agent Morwet D425 are charged in to the flask and refluxed under nitrogen, under stirring for 12-16hr. After the completion of the reaction, the reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried in water and then in IPA and isolated by filtration. The solid is dried at 95-1000C.Yield: 90 %; Purity: 100.30%

The chemical industry reduces the impact on the environment during synthesis 6-Chloro-5-(2-chloroethyl)indolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALKEM LABORATORIES LTD.; WO2009/116085; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 446292-08-6, 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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

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; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

2) A light yellow solid powder (compound represented by Structural Formula II) 74g was added to a 1000 ml round bottom flask.N-hydroxyethyl phthalimide 37.4g,Potassium carbonate 13g,N,N-dimethylformamide 1.3g,Methyl ethyl ketone 300g, stirring,Heating at 80 C reflux, the reaction for 8 h;After the reaction was completed, it was cooled to 40 C, 200 g of water was added, stirred for 1 h, filtered, and the filter cake was vacuum dried at 50 C for 12 h.87.7 g of a white solid powder (compound of formula III) was obtained.The crude yield was 95% and the purity was 97.932%.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Hydroxyethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Yuanshu Pharmaceutical Technology Co., Ltd.; Jin Feng; Zhou Taiyong; Wang Kai; Xiao Liang; Chun Qingyan; (11 pag.)CN109721587; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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.

Dissolve 2- (3-HYDROXYPROPYL) ISOINDOLE-1, 3-dione (2 g, 9.74 mmol, leq) in 40 mL of dichloromethane under N2. Add sulfuric acid (780 U. L) and cool reaction mixture to – 5C. Condense isobutylene gas to a liquid using a-78C cold finger charged with dry ice and acetone. Add approximately 20 mL of the condensed liquid to the reaction mixture and slowly warm the solution to room temperature overnight while stirring. Add saturated, aqueous sodium hydrogencarbonate to the reaction mixture and extract product into the organics. Wash separated organic layer with water and dry over magnesium sulfate to give 1.969 g (77% yield) of 2- (3-TERT-BUTOXYPROPYL) ISOINDOLE-1, 3-dione as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Hydroxypropyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/9941; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. Product Details of 20780-72-7

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

The synthetic route of 4-Bromoisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate

1.1 -dimethylethyl 4-fluoro-5-(4.4.5.5-tetrameth yl-1.3.2-dioxaborolan-2-yl)-2.3-dih vdro-1H- indole- 1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)-CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-Dioxane (20 mL) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 :1 NaCI(aq. sat.): H20, (100 mL) and ethyl acetate (100 mL), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0- 25% EtOAc in hexanes, 40 g silica gel column) to afford 1 ,1 -dimethylethyl 4-fluoro-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. 1H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1 .51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 – 7.61 (m, 2 H).

The synthetic route of 1337533-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-2-one, 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 13220-46-7, Recommanded Product: 13220-46-7

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 mL of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide. The mixture was stirred for 1 hour, diluted with 100 mL 50% acetic acid in water and filtered. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off-white solid.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem