Month: June 2021

Reference of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-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.

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent. Spiro[cyclopropane-1,3?-indoline]-2?-one (10a). Colorless crystalline (24 mg, 75 % yield). mp 177 – 180 C. Analytical data for 10a was consistent with that previously reported [10h]. 1H NMR (300 MHz, CDCl3): delta 8.94 (s, 1H), 7.16 – 7.26 (m, 1H), 6.97 – 7.00 (m, 2H), 6.84 (d, J=7.4Hz, 1H), 1.75 – 1.79 (m, 2H), 1.52 – 1.56 (m, 2H); delta13C NMR (75 MHz, CDCl3): delta 179.8, 140.8, 131.3, 126.8, 122.0, 118.6, 109.9, 27.6, 19.5. HRMS (ESI-TOF) calcd for C10H10NO [M+H] +: 160.0757; found: 160.0757.

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

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. SDS of cas: 16800-68-3

3 -propyl-propyne acid 4 – nitrophenyl-unitz (69.3 mg 0.3 mmol), was used. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 3h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 36 mg and gave rise 92% to unit_.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6326-79-0

To a suspension of 6-bromoisatin (Richman) (5.0 g, 22.1 mmol) in water (55 ml) was added [NAOH] (0.94 g, 23.5 mmol, 1.1 equiv) and the mixture was warmed to approximately [35 C] for 30 minutes to form a solution. The solution was cooled to [5 C] and a solution of sodium nitrite (1.70 g, 24.8 mmol, [1.] [1] equiv) was added dropwise over approximately 30 minutes, keeping the temperature below 10 C. The whole mixture was added dropwise via a cannula to a vigorously stirred solution of concentrated sulphuric acid (4.48 g, 45.7 mmol, 2.0 equiv) in water (55 ml) keeping the temperature below [10 C.] The mixture was stirred for 20 minutes and a solution of tin (II) chloride (10.2 g, 54.0 mmol, 2.4 equiv) in concentrated hydrochloric acid (21 ml) was added dropwise. The mixture was stirred at [5 C] for 2 hours and the resulting crude 5-methylindazole-3-carboxylic acid was isolated by filtration and washed several times with water. The yellow solid was then azeotroped with toluene (3 x 100 ml) to remove water prior to the next step to leave a yellow/green solid. LCMS MH+ 238/240 [(79BR/8LBR),] RT 2.69 min.

According to the analysis of related databases, 6326-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2004/14864; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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