Category: indolines-derivatives

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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., 446292-07-5

300 ml of THF were added to 20 g of 2-((2i?)-2-hydroxy-3-{ [4-(3-oxomorpholin-4- yl)phenyl]amino}propyl)- lH-isoindol-l ,3(2H)-dione (14, 0.0506 mol), 16 g of Iota , Gamma- carbonyldiimidazole (0.09869 mol) and 0.1 g of 4-dimethylamino)pyridine. The suspension was stirred and heated to boiling for 7 hours, then slightly cooled and another portion of Iota , Gamma-carbonyldiimidazole (0,09869 mol) was added. Then, the suspension was stirred under boiling for 14 hours. After that the mixture was cooled to 25C, which was followed by filtration, washing of the cake with THF, with an ethanol/water mixture (9: 1) and drying. 15.6kg of an off-white powder was obtained that melted at the temperature of 216 to 217C; HPLC 99.9%, content of the (R)- isomer below 0.03%, yield 73%.

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; ZENTIVA, K.S.; HALAMA, Ales; KRULIS, Radim; BRICHAC, Jiri; WO2013/120464; (2013); A1;,
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 317-20-4 as follows. 317-20-4

General procedure: To an aqueous mixture of 4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 3a (2 mmol), aldehyde 5 (2 mmol), malononitrile 4 (2 mmol) and piperidine (10 mol %) were added successively at room temperature under an open atmosphere with vigorous stirring. The progress of the reaction was monitored by thin layer chromatography. The precipitated solid was ltered, washed with water (10 mL) and ethanol (5 mL) and then with ether (3 mL). The product was dried under vacuum.

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jayarajan, Ramasamy; Vasuki, Gnanasambandam; Tetrahedron Letters; vol. 53; 24; (2012); p. 3044 – 3048;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2307-00-8

4-(3-Chloro-2-hydroxypropylamino)-N-methylphthalimide Twenty-five grams (g) (0.142 mole) 4-amino-N-methylphthalimide [Flitsch, Chem. Ber. 94:2494(1961)] and 20.7 g (0.21 mole) 1-chloro-2,3-epoxypropane were added to 150 ml 2,2,2-trifluoroethanol and the reaction mixture was heated to reflux with stirring for 48 hours. Seventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation and a heavy yellow precipitate formed when the remaining solution cooled to room temperature. This precipitate was triturated with ethyl acetate, collected by filtration and dried to give 29.5 g (77% yield) of the desired phthalimide intermediate m.p. 136-138.5 C. Analysis: Calculated for C12 H13 ClN2 O3: C, 53.64; H, 4.88; N, 10.45: Found: C, 53.87; H, 4.85; N, 10.81.

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, 2307-00-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Miles Laboratories, Inc.; US4363759; (1982); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1127-59-9 name is 7-Methylindoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 1127-59-9

General procedure: A solution of isatin derivatives 1 (0.4 mmol), 3-methyl-4-nitro-5-alkenyl-isoxazoles 2 (0.6 mmol) and proline or thioproline or sarcosine (0.8 mmol) in 10.0 mL of CH3CN at 80 ¡ãC for 24 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc5:1-3:1) to furnish the corresponding products 3-5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Liu, Xiong-Wei; Yao, Zhen; Yang, Jun; Chen, Zhi-Yong; Liu, Xiong-Li; Zhao, Zhi; Lu, Yi; Zhou, Ying; Cao, Yu; Tetrahedron; vol. 72; 10; (2016); p. 1364 – 1374;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

883-44-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 883-44-3 name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A 50 ml round bottom flask was charged with aq. NaHCO3(0.05 M, 10 ml), aq. K2CO3(0.5 M, 10 ml) and CHCl3(5 ml). Alcohol 5 (16.02 g, 78.1 mmol) was dissolved in CHCl3(50 ml) and transferred to the reaction mixture followed by tetra-nbutylammonium chloride (4.34 g, 15.6 mmol), N-chlorosuccinimide (20.9 g, 156.1 mmol) and TEMPO (2.44 g, 15.6 mmol) and the reaction mixture was stirred vigorously at rt for 4.5 h. The phases were separated and the organic phase was washed with sulfate buffer (100 ml), NaHCO3(100 ml), and brine (100 ml), dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (35% EtOAc in n-heptane, v/v) gave aldehyde 9 (6.54 g, 38%) as a white amorphous solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Hydroxypropyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Domeyer, Svenja; Bjerregaard, Mark; Johansson, Henrik; Pedersen, Daniel Sejer; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 644 – 647;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life. 317-20-4

EXAMPLES Example 1 Preparation of 7-Fluoro-1,3-dihydroindol-2-one; To a mixture of 7-fluoro-1H-indole-2,3-dione (100 g, 0.606 mol) in ethylene glycol (500 mL) was added an aqueous hydrazine solution (54% wt, 73 g, 1.21 mol) dropwise over 30 minutes. The mixture was heated to 120 C. and stirred for 6 hours. The mixture was cooled to room temperature and water (500 mL) was added. Concentrated hydrochloric acid (HCl; 60 mL) was added, the mixture was warmed to about 35 to about 40 C., and the mixture was stirred for 1 hour. The mixture was then cooled to about 0 to about 5 C. The solid compound was filtered, washed with cold water and dried at 55 C. under vacuum to give an off-white solid (76 g) in 83% yield with 96% HPLC purity.

The chemical industry reduces the impact on the environment during synthesis 317-20-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2007/27327; (2007); A1;,
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 3416-57-7 as follows. 3416-57-7

[00653] To a mixture of 89 (4.00 g, 19.7 mmol, 1.0 eq), 4-methylbenzenesulfonic acid (1.02 g, 5.91 mmol, 0.3 eq) and ethane-1,2-diol (20 mL) in toluene (20 mL) was stirred at 110 C overnight under nitrogen. The mixture was concentrated and the residue was purified by SGC (petroleum ether / ethyl acetate, 5 / 1) to afford the desired product 90 (2.90 g, 11.7 mmol, 59.5%) as a white solid.[00654] LCMS: ESI-MS: m/z: 248.2 [M+H1 RT = 1.49 mm. (Method A)

According to the analysis of related databases, 3416-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALPHARMAGEN, LLC; PUTMAN, David, G.; DASSE, Olivier; HOGENKAMP, Derk; (154 pag.)WO2016/144792; (2016); A1;,
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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 4702-13-0

To a solution of phthaloylglycin (0.300 g, 1.46 mmol) in CH2Cl2 was added oxalyl chloride (1.480 g, 11.66 mmol) and DMF (0.010 g, 0.137 mmol) at 0 C. The mixture was stirred at 0 C for 30 min., then warmed to room temperature and stirred for 3 h. The solvent was removed under reduced pressure. The solid residue was dissolved in CH2Cl2 and evaporated under reduced pressure (this procedure was repeated three times). The crude product was dried under vacuum to afford a yellow sold (0.310 g, 95%). This compound was used for next reaction without further purification.1H NMR (500 MHz, CDCl3). delta 7.91 (dd, J = 5.5, 3.2 Hz, 2H), 7.79 (dd, J = 5.5, 3.1 Hz, 2H), 4.82 (s, 2H).

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 496-12-8, name is Isoindoline, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 496-12-8

General procedure: To a solution of compound 5 (1.0eq.) and Ia-f (1.0eq.) was added K2CO3 (2.2eq.) in anhydrous DMF at RT. After stirring for 5-7h, the reaction was diluted with water and the precipitation was filtered to afford the crude targets. Then the crude target was purified by flash column chromatography (EtOAc : PE=1 : 5) to afford the compounds 6a-f. Targets 7a-e, 8a-d and 9a-c were obtained as the procedure for 6a-f by the reaction of compound 5 witha-e, IIIa-d and IVa-c.

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, 496-12-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Apeng; Yang, Yang; Jun, Yangsheng; Wang, Bin; Lv, Kai; Liu, Mingliang; Guo, Huiyuan; Lu, Yu; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2073 – 2084;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, 2058-72-2

General procedure: The reactions are conducted in a custom made, twelve membered carousal containing glass reaction chambered of 20 ml volume. To the stirred solution of 6-methylfuro[3,4-c]pyridine-3,4(1H,5H)-dione(200 mg, mmole) (1 equivalence) in ethanol (10 ml) , piperidine/pyrrolidine(1 equivalence) was added. To the stirring solution appropriateisatins (1.1 equivalence) were added under nitrogen atmosphere andthe resulting reaction mixture was refluxed at 80 C for 14 h (within which substantial amount of product precipitates from the reaction mixture). Then reaction mixture was cooled to room temperature and the supernatant was syringed off dissolved in ethyl acetate (10 ml) and washed with water. The organic layer was dried over Na2SO4, evaporated to obtain the crude which was purified by flash column chromatography with ethyl acetate/hexane as eluent.

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, 5-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Luthra, Tania; Naga Lalitha; Uma; Sen, Subhabrata; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4996 – 5005;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem