Month: April 2021

Reference of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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) Step 1 Aqueous sodium hydroxide (0.0888 g, 2.22 mmol, 2 mL) was heated to 50C, and added with 5-trifluoromethoxyisatin (0.500 g, 2.16 mmol). The mixture was stirred at 50C for 1 hour, and then cooled on ice. The reaction mixture was added with sodium nitrite (0.149 g, 2.16 mmol), and then added dropwise with a solution of concentrated sulfuric acid (0.413 g, 4.21 mmol) in ice-cooled water (3.5 mL), and the mixture was stirred for 1 hour under ice cooling. Then, the mixture was added dropwise with an ice-cooled solution of tin(II) chloride dihydrate (1.17 g, 5.18 mmol) in concentrated hydrochloric acid (1.7 mL). The mixture was stirred overnight at room temperature, and then filtered to obtain a pale brown solid (0.638 g).

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-Nitroindoline, 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 19727-83-4, Recommanded Product: 6-Nitroindoline

At room temperature, 6-nitroindoline (99 mg, 0.6 mmol) was added to the reaction tube containing p-methylthiophenol (62 mg, 0.5 mmol) and dimethyl sulfoxide (1.0 mL). After stirring uniformly at room temperature, riboflavin 1 (0.025 mmol, 8 mg) and elemental iodine (0.05 mmol, 13 mg) were added in sequence, and then vacuum oxygen protection was applied. After the reaction tube was reacted at 60C for 24 hours, it was cooled to room temperature, and saturated sodium thiosulfate solution was added to quench the reaction. Then, the reaction solution was extracted with ethyl acetate, and then washed with saturated sodium chloride solution, and the organic layers were combined and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation.Finally, it was purified by column chromatography (n-hexane: ethyl acetate = 30: 1) to obtain a yellow solid 6-nitro-3-(4-methylphenylthio)indole 106 mg, yield 75%.

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; Zhejiang University of Technology; Jiang Xinpeng; Zhao Zongchen; Yu Chuanming; (8 pag.)CN111100056; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

[0195] To 2,3-dihydro-isoindol-l-one (250.Omg, 1.85mmol) in acetonitrile (9mL) was added propargyl bromide (308.6uL, 2.77mmol) and cesium carbonate (2.4g, 7.39mmol) and the mixture was allowed to stir at 80C for two hours. An aqueous workup was done to provide the title compound (303.3mg, 96%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); 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. 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

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Quality Control of Isoindoline

The above compound was prepared as follows using General Procedure G9. lsoindoline (130 mg, 1 mmol) was added to a solution of 3-chloro-4,6-dimethoxy-2- methylbenzoic acid (compound A in general procedure G9, and prepared via the method reported by Clevenger et al. Organic Letters (2004), 6(24), p4459)) (200 mg, 0.87 mmole), diisopropylethyl amine (0.8 mL, 4.5 mmol), and O-(7-azabenzotriazol-1 -yl)-N,N,N’,N’- tetramethyluronium phosphorus pentafloride (HATU) (380 mg, 1 mmol) in 4 mL of DMF under a nitrogen atmosphere. The reaction was allowed to stir at room temperature for 12 hours. Saturated NaHCO3 (30 mL) was added to the reaction mixture to quench the reaction. EtOAc EPO (2 x 50 ml.) was then added to extract the aqueous solution. Dry EtOAc layer over Na2SO4. The Na2SO4 was filtered off and the filtrate was evaporated to give a brown oil residue. The residue was purified by silica gel chromatography (gradient elution 45 ?50% EtOAc in hexanes) to give the desired intermediate product (3-chloro-4,6-dimethoxy-2- methylphenyl)(isoindolin-2-yl)methanone (265 mg, 92% yield). 1H NMR (400 MHz, DMS0-D6) delta ppm 2.18 (s, 3 H) 3.81 (s, 3 H) 3.92 (s, 3 H) 4.39 (d, J=7.07 Hz, 2 H) 4.80 (s, 2 H) 6.76 (s, 1 H) 7.17 – 7.35 (m, 3 H) 7.38 (d, J=7.07 Hz, 1 H): Anal. Calcd for C18H18CINO3: C, 65.16; H, 5.47; N, 4.22. Found: C, 65.05; H, 5.48; N, 4.22.

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2006/117669; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6341-92-0, 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 6341-92-0 as follows.

Step 1 2-( -amino-3-chlorophenyl)-7-chloroquinoline-4-carboxylic acid [00425] A solution of l-(4-amino-3-chlorophenyl)ethan-l-one (4.2 g, 24.9 mmol) in EtOH (20 mL) was added to a solution of 6-chloroindoline-2,3-dione (3 g, 16.6 mmol) in 6 M aqueous KOH (20 mL) at 100C. The reaction was monitored by LC-MS until the starting material consumed. Then the reaction mixture was concentrated to remove EtOH, then adjusted the pH to 4-5. The precipitate was filtered to give the desired product 2-(4-amino-3-chlorophenyl)-7- chloroquinoline-4-carboxylic acid (4.1 g, 74.5%) as red solid.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEW YORK UNIVERSITY; UNIVERSITY OF ALBANY; SCHMIDT, Ann, Marie; RAMASAMY, Ravichandran; SHEKHTMAN, Alexander; RAI, Vivek; MANIGRASSO, Michaele, B.; (179 pag.)WO2017/184547; (2017); 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

2-Phthalimidoethanol lNo.,lNo.,2No.,2No.-perfluorodecylsulfonate (23) ;hi a 10 mL round bottomed flask, distilled triethylamine (84 muL, 0.60 mmol) followed by lH,lH,2H,2H-perfluorodecyl sulfonyl chloride (328 mg, 0.60 mmol) were added to a stirred solution of N-(2-hydroxyethyi)phthalimide (96 mg, 0.50 mmol) in DCM (3 mL) at O0C under a nitrogen atmosphere. The mixture was allowed to stir for 3 hours whilst warming up to room temperature before being quenched with sodium carbonate solution and extracted with DCM (3 x 10 mL). The combined organic phases were washed with brine, dried over MgSO4, and the solvent removed under reduced pressure. The crude solid was washed with Et2O to afford the target compound as a white solid (256 mg, 0.366 mmol, 73% 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.

Reference:
Patent; ISIS INNOVATION LIMITED; GOUVERNEUR, Veronique; BEJOT, Romain; WO2010/7363; (2010); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-1-one, 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. HPLC of Formula: C8H6N2O3

6-Nitro-2,3-dihydroisoindol-1-one (4.7 g, 26 mmol) was dissolved in acetic acid (130 ml) and hydrogenated at 50 psi (3 bar) in the presence of palladium on charcoal (0.47 g) overnight. The catalyst was filtered off through a pad of Hyflo and the acetic acid was removed in vacuo. The residue was triturated with dichloromethane/hexane and the resulting solid was filtered off to afford the title compound (3.56 g, 91%). 1H NMR (360 MHz, d6 DMSO) X 8.28 (1H, s), 7.17 (1H, d, J=8 Hz), 6.82 (1H, s), 6.78 (1H, dd, J=8.1, 1.8 Hz), 5.25 (2H, s), 4.16 (2H, s). m/z (ES+) 149 (M+H)+.

The synthetic route of 6-Nitroisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); 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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 61-70-1

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 317-20-4

STEP C: 2-amino-3-fluoro-benzoic acid A mixture of 19.27 g of the product of Step B and 197 ml of 10N sodium hydroxide solution was heated to 70 C. with stirring and heating was ceased to add 36.5 ml of 30% hydrogen peroxide over 20 minutes during which the temperature rose to 80 C. and descended to 70 C. At the end of the addition, the mixture was heated to 80 C. and held there for 10 minutes and then was cooled during which a mass formed. The latter was added to 200 ml of water with stirring and the pH was adjusted to 1 by addition of concentrated hydrochloric acid at a temperature less than 20 C. The mixture was stirred for 90 minutes and was vacuum filtered. The product was empasted twice with iced water and dried under reduced pressure at 70 C. The product was crystallized from 100 ml of a 1-1 ethanol-water mixture and 3 ml of acetic acid. The mixture was iced for one hour and was vacuum filtered. The product was empasted with a 1-1 ethanol-water mixture and dried at 70 C. under reduced pressure to obtain 14.8 g of 2-amino-3-fluoro-benzoic acid melting at 188 C.

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; Roussel Uclaf; US4736033; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem