Indolines-derivatives

Application of 71294-03-6, 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. 71294-03-6 name is 7-Fluoroindolin-2-one, 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.

7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) was dissolved in THF (200 mL). The solution was then cooled to -78 C. and n-butyllithium (2.5 M, 40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate, dried (MgSO4), and concentrated in vacuo. Flash chromatography (SiO2, Hexane/ethylacetate 9/1 then 8/2) gave 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g, 48%)

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

Reference:
Patent; Wyeth; US2006/9509; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-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 18711-13-2, Product Details of 18711-13-2

General procedure: To the stirred solution of beta-keto ester 2(aei) (1.0 mmol) and DABCO (30 mol %) in 5 mL THF was added isatin 1(aeh) (1 mmol).The mixture was then stirred at room temperature for stipulated time (5-8 h). After completion of reaction as indicated by TLC, thesolvent was removed at reduced pressure on a BUCHI rotary evaporator. The residue was then purified by column chromatography on silica gel (hexane/ethyl acetate4:1 to 1:1) to afford thedesired product 3(a-w).

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, 4,7-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thakur, Pramod Bhagwan; Sirisha, Katukuri; Sarma, Akella Venkata Subrahmanya; Nanubolu, Jagadeesh Babu; Meshram, Harshadas Mitaram; Tetrahedron; vol. 69; 31; (2013); p. 6415 – 6423;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 39603-24-2

General procedure: A mixture of isatins 1c, e-g (1 mmoL) with an equimolar amount of 2-mercaptobenzimidazole6 (0.15 gm, 1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in thepresence of sodium acetate (0.16 g, 2 mmoL), was heated under reflux for 2 h. The obtained solid wasfiltered off while hot, washed with hot ethanol, dried and recrystallized from DMF to afford the targethybrids 7a-d.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39603-24-2, its application will become more common.

Reference:
Article; El-Naggar, Mohamed; Eldehna, Wagdy M.; Almahli, Hadia; Elgez, Amr; Fares, Mohamed; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Molecules; vol. 23; 6; (2018);,
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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6BrNO2

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 mol%) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

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; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

PREPARATION 10; 6-Chloro-5- (3-chloro-propionyl)-1, 3-dihvdro-indol-2-one; A 500mL RB flask equipped with a stirrer, reflux condenser and heating mantle, was charged with aluminum chloride (AICI3) (14.76 g, 0.11 mol), 75 mL of carbon disulfide and 3-chloropropionyl chloride (2.21 mL, 0.023 mol) and this was stirred at rt during the portionwise addition of 6-chloro oxindol (3.0 g, 0.0179 mol). This mixture was then heated to reflux for 3 hours, then cooled. The solvent was decanted and the reaction was quenched with addition of ice and water. The suspension was stirred vigorously for 0.5 hours, followed by filtration. The solids were washed with water and then dried overnight in a vacuum oven. Yield = 4.23 g (92%); MS (APCI), (M + 1) + = 259. 1.

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, 6-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/66165; (2005); 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. 153171-22-3, name is 2-(4-Bromobenzyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(4-Bromobenzyl)isoindoline-1,3-dione

(b) The reaction mixture of 2-(4-bromobenzyl)isoindole-1,3-dione (5.01g, 15.83mmol) and H2NNH2·H2O (100%) (1.59g, 31.67mmol) in MeOH (50ml) was stirred for 1h at reflux. After cooling, MeOH was removed under reduced pressure. Concentrated HCl (20ml) was then added and the resulting mixture was stirred for 1.5h at reflux. After cooling, 2N NaOH (200ml) was added to the mixture, and the insoluble matters were removed by filtration. The filtrate was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and then brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford 4-bromobenzylamine (2.73g, 14.65mmol, y. 93%) as a yellow oil. 1H NMR (300MHz/CDCl3) delta 3.83 (2H, s, CH2), 7.20 (2H, d, J=8.4Hz, ArH), 7.45 (2H, d, J=8.4Hz, ArH).

The synthetic route of 153171-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3720 – 3731;,
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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C9H6BrNO2

General procedure: S-alkylation of the products was achieved by following a modified method [38]. The oxadiazoles (6a, 6b, 13) (0.02, mol) and K2CO3 (0.022, mol) were stirred in 10mL of acetone for 20 mints followed by the addition of alkyl bromides 7a-c and 7d-m (0.022, mol). The reaction mixture was stirred for 4-6h at room temperature. The reaction mixture was concentrated under vacuum and crude solid gained was recrystallized from methanol to get pure products.

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; Batool, Farwa; Hamdani, Syeda Shamila; Hameed, Shahid; Khan, Bilal Ahmad; Mughal, Ehsan Ullah; Saeed, Muhammad; Saleem, Hafiza Nosheen; Bioorganic Chemistry; vol. 96; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 18711-15-4,Some common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, 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.

Step 3 Preparation of 2-amino-4,6-dichlorobenzoic acid To a solution of 4,6-dihloro-1H-indole-2,3-dione (5.0 g, 23.1 mmol) in 75 ml of 1 N NaOH was partially added hydrogen peroxide (28% v/v, 10 ml) at room temperature. After stirring the mixture for 2 hours, an insoluble dark brown solid was removed by filtration. The filtrate was acidified with a cone, hydrochloric acid to a pH of 2. The yellow precipitate thus formed was harvested, washed with distilled water, and dried in a vacuum. Recrystallization in benzene produced the title compound as an ivory solid (3.90 g, 82%). TLC Rf=0.1 (ethylacetate: n-hexane=1:1); m.p. 188-189 C.; 1H NMR (DMSO-d6) delta 6.76 (d, 1H, J=1.9 Hz, ArH), 6.85 (d, 1H, J=1.9 Hz, ArH); MS (EI) m/e 206 [M+], 162 [M+-CO2].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,6-Dichloroisatin, its application will become more common.

Reference:
Patent; Korea Research Institute of Chemical Technology; US2009/203708; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 496-12-8, name is Isoindoline, 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. Computed Properties of C8H9N

Intermediate 5A 2-(4-bromo-3-fluorophenyl)-1-(isoindolin-2-yl)ethanone [0492] [0493] To a mixture of 2-(4-bromo-3-fluorophenyl)acetic acid (300 mg, 1.287 mmol), isoindoline (0.161 mL, 1.416 mmol), and HATU (734 mg, 1.931 mmol) in DMF (5 mL), was add DIEA (0.450 mL, 2.6 mmol). The mixture was stirred rt for 18 h. The reaction mixture was diluted with EtOAc, then was washed with H2O, 1N HCl, H2O, sat. Na2CO3 and brine. The organic phase was dried (Na2SO4), filtered through a 1? pad of SiO2 and concentrated. The crude product was purified by flash chromatography (gradient from 0 to 100% ethyl acetate/hexanes) to afford 379 mg (88%) of Intermediate 5A as an off-white solid. MS (ESI) m/z: 333.9 (M+H)+; 1H NMR (400 MHz, CDCl3) delta 7.50 (dd, J=8.0, 7.4 Hz, 1H), 7.33-7.22 (m, 4H), 7.14 (dd, J=9.2, 2.0 Hz, 1H), 7.01 (dd, J=8.5, 1.9 Hz, 1H), 4.83 (s, 4H), 3.72 (s, 2H)

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

Reference:
Patent; Glunz, Peter W.; Zou, Yan; Quan, Mimi L.; US2014/206686; (2014); 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6N2O2

EXAMPLE 8 The steps followed in the procedure of this example are illustrated diagrammatically below: STR6 Step (a), Production of 5-Aminophthalide Twenty grams of 4-aminophthalimide was added to a mixture of 41 gm zinc and 122 gm sodium hydroxide in 50 ml water (with good stirring) over 30 minutes. The mixture was stirred another 30 minutes, then heated to 60. When ammonia ceased to be evolved the mixture was heated for an additional 60 minutes, then cooled to about 30. The zinc residues were filtered off and the solution was acidified with 30 ml concentrated hydrochloric acid. The solution was heated to 90 for 45 minutes, then cooled and neutralized with 20 gm solid sodium carbonate, which brought the pH to 8-9. The product was filtered, washed with water and air dried. Wt=16.8 gm, m.p.=177-189.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pennwalt Corporation; US4665181; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem