Tag: M.W=100-200

Electric Literature of 172078-33-0,Some common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, molecular formula is C8H9NO, 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.

To a stirred solution of 6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-l-(pyri- din-2-ylmethyl)-l,2-dihydroquinoline-3-carbaldehyde (intermediate- le) (0.2 g, 0.51 mmol) in titanium isopropoxide (5 mL) was added indolin-5-ol (0.1 g, 0.77 mmol) followed by stirring at RT for 16 h. After stirring, methanol (20 mL) was added to the mixture at 0 C followed by NaCNBH4 (0.16 g, 2.56 mmol). The mixture was stirred at RT for 2 h. The mixture was then quenched with ammonium hydroxide and the solids were filtered off. The filtrate was extracted with EtOAc (100 mL x 2), washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified to get the title compound as pale brown solid (0.016 g, 6 %). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J=4.8 Hz, 1H), 7.86 (s, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.23-7.20 (m, 2H), 6.69 (s, 1H), 6.60-6.48 (m, 2H), 5.74 (s, 2H), 4.29 (s, 2H), 3.79 (s, 3H), 3.61-3.59 (m, 2H), 3.10-3.00 (m, 2H), 2.25 (s, 3H), 2.11 (s, 3H); LC-MS: m/z 509.3 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-5-ol, its application will become more common.

Reference:
Patent; ORION CORPORATION; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; LINNANEN, Tero; WOHLFAHRT, Gerd; (120 pag.)WO2017/1733; (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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A mixture of dibromoalkane (23 mmol) and potassium carbonate (12 mmol)was added in acetone (30 mL), and potassium phthalimide (10 mmol) was added slowly over a 15-min period, and then the reaction was heated under reflux for 8-10 h. The reaction mixture was filtered,and the acetone was evaporated in vacuo. The crude product was purified by column chromatography on silica gel using mixtures of petroleum/acetone as eluent) to obtain the white solid compounds 2-4.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 60434-13-1, 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure forthe preparation of oxazolo[5,4-b]quinoline- fused spirooxindoles 4a-t: A reaction of isatin(1 mmol),beta-diketone (1 mmol) and5-amino-3-methylisoxazole (1 mmol) were mixed and irradiated in a closed vesselin the absence of any solvent in a Synthos 3000 microwave reactor at 700 W, 14 bar,and 110 C for 10 min. The reaction was monitored by TLC. Then, thereaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuvaraj, Panneerselvam; Manivannan, Karthikeyan; Reddy, Boreddy S.R.; Tetrahedron Letters; vol. 56; 1; (2015); p. 78 – 81;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 64483-69-8, 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. 64483-69-8, name is 5-Acetylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

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-Acetylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 60434-13-1, 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. 60434-13-1 name is 5-Chloro-1-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.

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
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, COA of Formula: C8H6ClNO

A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added to a solution of 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) in tetrahydrofuran(5mL) under argon atmosphere, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6):delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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; Institute of Medicinal Molecular Design, Inc.; EP1535609; (2005); A1;,
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. 86626-38-2, name is 4-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromoindoline

To a solution of 4-bromoindoline (12.2 g, 61.6 mmol) in dichloromethane (200 mL) was added Boc20 (14.8 g, 67.8 mmol) and DMAP (0.75 g, 6.16 mmol). The mixture was stirred at room temperature for 48 h and then evaporated. The residue was purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to provide the title compound (11.5 g, 62.5%). 1H NMR (CDC13) delta: 7.80 (br. s, 1H), 6.98-7.12 (m, 2H), 4.00 (t, J=8.7 Hz, 2H), 3.08 (t, J=8.7 Hz, 2H), 1.50-1.66 (s, 9H).

According to the analysis of related databases, 86626-38-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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 19155-24-9, Product Details of 19155-24-9

3,3-Dimethyl-1,3-dihydro-indol-2-one (5.5 g, 34 mmol) was dissolved in dimethylformamide (50 mL) and sodium hydride (1.4 g, 38 mmol) was added portionwise and the mixture was stirred 30 minutes then benzyl bromide (4.8 mL, 41 mmol) was added. The mixture was stirred 2 hours then quenched with saturated aqueous ammonium chloride, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 0-20percent ethyl acetate in hexane) to afford 7.1 g (83percent) of 1-benzyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. HPLC purity 96.4percent at 210-370 nm, 9.5 minutes; Xterra RP18, 3.5u, 150*4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 minutes, hold 4 minutes. HRMS: calculated for C17H17NO+H+, 252.13829; found (ESI, [M+H]+), 252.142

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

Reference:
Patent; Wyeth; US2007/72928; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, 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. Quality Control of 5-Methoxyisoindoline-1,3-dione

A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at 00C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to 0C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSO-d6) 7.13 (1 H, d), 6.84 (1H1 d), 6.74 (1H, dd), 4.05 (2H, s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.

The synthetic route of 5-Methoxyisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); 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 16800-68-3 as follows. category: indolines-derivatives

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem