Author: tianli

These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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. SDS of cas: 14192-26-8

To a solution of methyl 2-oxoindoline-6-carboxylate (17.6 g) in DMF (260 ml) was added Mel (26.1 g) followed by NaH (3.68 g) keeping the temperature at 22 C. After 30 min a second portion of NaH (1.84 g) was added followed after 1 h by a third portion (1.84 g) and stirring was continued at 22 C for 16 h. Water (7 ml) followed by sodium hydroxide (34.5 g) were added and stirring was continued at 45 C for 1 h and at 22 C for 16 h. The mixture was partitioned between TBME and water, the pH of the aqueous layer was adjusted to 3 using aqueous hydrochloric acid (25%) and extracted with dichloromethane. The organic layere was dried and evaporated to give the crude title compound (17.9 g, 95%) as a red solid, which was used without further purification. MS (ESI, m/z): 204.2 [(M-H)”].

The synthetic route of Methyl 2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is Indolin-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 59-48-3, Formula: C8H7NO

Concentrated nitric acid (9.31 g, 0.096 mol) was added in drops over 60 min and at 0 C. to a solution of indolin-2-one (13.3 g, 0.100 mol) in concentrated sulfuric acid (67 mL), and the resultant dark-brown solution was then stirred at this temperature for 1 h. The reaction mixture was then poured over ice and sucked away. The residue was washed again with water and dried, then recrystallized from isopropanol. 5-nitroindolin-2-one in the form of golden, shiny sheets was obtained (12.28 g, 69%). fp: >300 C. 1HNMR (300 MHz, d6-DMSO): delta=3.61 (s, 2H, H2), 6.97 (d, 1H, H7), 8.05 (d, 1H, H6), 8.05 (s, 1H, H4), 8.15 (d, 1H, H6), 11.03 (bs, 1H, NH). 13C NMR (100 MHz, DMSO): 35.9 (C2), 109.2 (C7), 120.3 (C4), 125.1 (C6), 127.2 (C9), 142.0 (C5), 150.6 (C8), 177.0 (C2)

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; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-oxoindoline-6-carboxylate

Intermediate Ia (4Og) is dissolved in methanol (40OmL) and IM NaOH solution (420 mL) is added. The mixture is heated under reflux for 3 hours. The reaction is then neutralized with IM HCl. The methanol is then removed under reduced pressure and water is added EPO until precipitation commenced. The precipitate is collected via filtration, washed with water and dried under reduced pressure to yield the desired intermediate 2a (37g)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14192-26-8.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Methoxyisatin

Preparation of 5-methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)-indole-3-carbaldehyde; 5-Methoxy isatin (0.2 g, 1.1 mmol, 1 eq.) was dissolved in hydrazine hydrate (1.2 ml_, 38 mmol, 34 eq.) and refluxed for 15 minutes. The reaction mixture was poured into cold water and extracted with EtOAc. The combined organic extracts were dried on Na2SO4. The solvent was evaporated to afford crude 5-methoxy-1 ,3-dihydro-indol-2-one that was purified by silica gel column chromatography (eluent: hexane/EtOAc from 10:0 to 6:4). Yield: 27%. MS (m/z): 164.2 (MH+).Phosphorous oxybromide (0.35 ml_, 3.1 mmol, 2.5 eq.) was added drop wise to a solution of DMF (0.3 ml_, 3.7 mmol, 3 eq.) in dry methylene chloride at 00C. The mixture was stirred at 00C for 30 minutes, then a solution of 5-methoxy-1 ,3-dihydro-indol-2-one (0.2 g, 1.2 mmol, 1 eq.) in dry methylene chloride (2 ml_) was added and the mixture was refluxed for 3 hours. The solution was neutralized with solid NaHCO3 and extracted with methylene chloride. The organic layer was dried on Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by silica gel column chromatography (eluent: hexane/AcOEt 6:4 to 4:6) to give pure 2-bromo-5-methoxy-indole-3-carbaldehyde. Yield: 45%. MS (m/z): 254.1 (MH+). A stirred solution of 2-bromo-5-methoxy-indole-3-carbaldehyde (2.0 g, 7.9 mmol, 1 eq.) in DME (2 ml_) was deoxygenated by bubbling argon for 10 minutes at rt. Pd(PPh3)4 (0.9 g, 0.8 mmol, 0.1 eq.) was added followed by a solution of 1-methyl-4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazole (2.4 g, 1 1.63 mmol, 1.48 eq.) in ethanol (2.5 ml_). 2M Na2CO3 (33 ml_, 8.5 eq.) was also deoxygenated with argon and added. The resulting mixture was heated at 78C for 18 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted with methylene chloride. Organic layer was dried on anhydrous Na2SO4 and evaporated under reduced pressure to give the crude product 1f. Yield: 89%. MS (m/z): 256.1 (MH+).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.; WO2010/30727; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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. category: indolines-derivatives

General procedure: The isatin ( 0.01 mol scale) was dissolved in 50 ml of CH3OH in a 150 ml round bottomed flask equipped with a reflux condenser and a stir bar. The mixture was brought to reflux that was followed by gradual addition of KBH4 (0.27 g, 0.005 mol). The reaction mixture continued to stir under reflux for 1 hour. While heating, the stopper of the round bottomed flask was removed 2-3 times and the flask was shaken to saturate the reaction mixture with air. After 1 hour, the solution was cooled to room temperature and the indirubin precipitated out of the solution. The solid was isolated by filtration and was further purified by recrystallization from 95% C2H5OH or by column chromatograph on silica gel. Indirubin and 10 indirubin derivatives in Z form were synthesized by this method. The structures of the indirubins were determined by 1H NMR, 13C NMR, MS, IR, UV and elemental analysis, and the stereochemistry was assigned by comparing the spectra data to published reports or comparing to authentic samples.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Cuiling; Yan, Jiaxu; Du, Mo; Burlison, Joseph A.; Li, Chi; Sun, Yanni; Zhao, Danqing; Liu, Jianli; Tetrahedron; vol. 73; 19; (2017); p. 2780 – 2785;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(2- bromoethoxy)isoindoline- l,3-dione (5 g, 1.85 mmol, product from step 1 of preparation 10) and lH-tetrazole (1.3 g, 1.85 mmol) in dimethylformamide (25 ml) was added cesium carbonate (6.0 g, 1.85 mmol) in a lot wise under stirring at room temperature. The progress of reaction was monitored by performing thin layer chromatography using mixture of acetone and hexane (3.5:6.5) as solvent. After 16 hours the completion of the reaction was confirmed by thin layer chromatography. The reaction mixture was slowly poured into chilled water (200 ml) under stirring. After stirring for 30 minutes, the precipitates formed were filtered and washed with water (50 ml). The solid compound was dried at 40 C for 2 hours under high vacuum to provide 3.2 g of a mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2-(2H-tetrazol-2- yl)ethoxy]- lH-isoindole- l,3(2H)-dione in 66% 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-(2-Bromoethoxy)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H7NO2

A 20-mL, microwave reaction vessel was charged with (3-bromopyridin-4-yl)-(4-(trifluoro methyl)phenyl)methanol (2.0 g, 6.02 mmol), 2-vinylisoindoline-1,3-dione (1.16 g, 6.68 mmol), 2-(dicyclohexylphosphino)biphenyl (0.211 g, 0.60 mmol), Pd(dba)2 (0.176 g, 0.30 mmol), NEt3 (1.0 mL, 7.23 mmol), and DMF. The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The brown residue was triturated with DCM, the resulting precipitate was collected by filtration to afford the title compound as an ivory colored solid. 1H NMR (400 MHz, CDCl3): delta 8.70 (s, 1H), 8.58 (d, J= 5.1 Hz, 1H), 7.92-7.95 (m, 2H), 7.79-7.7.84 (m, 3H), 7.55-7.64 (m, 5H), 7.24 (s, 0.5H), 7.19 (s, 0.5H), 2.71 (d, J= 3.4 Hz, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3485-84-5.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, 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.

General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylindolin-2-one, its application will become more common.

Reference:
Article; Delong, Wang; Lanying, Wang; Yongling, Wu; Shuang, Song; Juntao, Feng; Xing, Zhang; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 286 – 307;,
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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 675109-26-9

[1532] to a solution of 6-bromoisoindolin-1-one (0.5 g, 2.36 mmol) in acetone (20 ml) was added bnbr (605 mg, 3.54 mmol, 0.420 ml),Cs2CO3 (1.92 g, 5.90 mmol) and 18- crown-6 (62 mg, 235.80 umol), then the mixture was stirred at 70 C for 16h. The reaction mixture was concentrated to remove solvent, then diluted with water (50 ml) and extracted with ea (40 ml x 2), and the organic layers were dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by flash silica gel chromatography (isco; 12 g sepaflash silica flash column, eluent of 0-20% ethyl acetate/petroleum ethergradient 30 ml/min). Compound 378a (0.46 g, yield: 59.5%) was obtained as white solid. 1H NMR (400mhz, CDCl3) delta 8.02 (d, j = 1.8 hz, 1h), 7.63 (dd, j = 1.9, 8.0 hz, 1h), 7.39 – 7.16 (m, 6h), 4.79 (s, 2h), 4.21 (s, 2h). MS (ESI) m/z (M+H)+ 302.0.

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; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1677-48-1, name is 5,6-Dichloroindoline-2,3-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 1677-48-1, Recommanded Product: 5,6-Dichloroindoline-2,3-dione

General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dichloroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur; Indian Journal of Heterocyclic Chemistry; vol. 23; 4; (2014); p. 411 – 418;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem