Category: indolines-derivatives

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

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(2-Oxopropyl)isoindoline-1,3-dione

EXAMPLE 1 Phthalimidoacetone ethylene ketal A solution of phthalimidoacetone 61.9 g (300 mmole) and ethylene glycol 18.9 g (300 mmole) in 300 ml of benzene in the presence of concentrated sulfuric acid (1 drop) is refluxed with stirring for 24 hours. An additional portion of ethylene glycol (18.9 g., 300 mmole) and p-toluenesulfonic acid (3 mg) is added and refluxing is continued for 65 hours. The reaction mixture is cooled in ice, washed with saturated sodiumchloride solution and dried over anhydrous sodium sulfate. The benzene is removed in vacuo and the residue is crystallized from methanol to give 67 g (90%) of phthalimidoacetone, ethylene ketal as white prisms of melting point 92-94 C.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Upjohn Company; US3992408; (1976); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-1-one, molecular formula is C8H6N2O3, 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 110568-64-4

To a solution of 5-nitro-2,3-dihydro-1H-isoindol-1-one (60 mg, 0.337 mmol) in methanol (20 mL) was added 50 mg of 10percent Pd on carbon. The mixture was hydrogenated (with a balloon) for 1 hour. Filtration through Celite.(TM). followed by concentration led to 38 mg of 5-amino-2,3-dihydro-1H-isoindol-1-one as a tan solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 110568-64-4, its application will become more common.

Reference:
Patent; Wyeth; US2010/15141; (2010); 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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Oxindole (1.30 g, 0.010 mmol) was suspended in dry acetonitrile (22.0 mL) under N2 and cooled to -10 C. To this stirred mixture was added recrystallized NBS (2.00 g, 0.011 mol) portionwise. The resulting suspension was stirred at -10 to 10 C. for 3 h. The precipitated solid was collected by filtration, washed with H2O and dried to give the intermediate title compound as an off white solid 1.75 g (82%). Electrospray mass spectrum (M-1)=210, (M-1)=211

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; Eli Lilly and Company; US7034045; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H8N2O2

To a solution of 5-nitroindoline (11.72 g) and triethylamine (8.67 g) in N, N-dimethylformamide (150 ml) was added dropwise chloroacetyl chloride (8.06 g) at 5C and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured into a mixture of ethyl acetate and water and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ethyl acetate and collected by filtration to give 1- (CHLOROACETYL)-5-NITROINDOLINE (14.66 g) as a yellow crystal. 1H-NMR (DMSO-d6): 8 3. 28 (2H, t, J=8.6 Hz), 4.25 (2H, t, J=8.6 HZ), 4.64 (2H, s), 8.1-8. 2 (3H, m) ESI-MS (m/z): 263 (M+Na) +

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem