Month: April 2021

Related Products of 3676-85-5, 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 3676-85-5 as follows.

To a solution of intermediate compound 3 (0.037 mol) in 20 ml of concentrated hydrochloric acid was added slowly to a solution of sodium nitrite (0.039 mol) in 15 ml of water under ice-cooling. The temperature of the control solution was not more than 5 C. After adding, the mixture was stirred for 30 minutes under ice bath, and the insoluble matter was filtered off. The filtrate was slowly added to a mixture of cuprous chloride (0.3737 mol) in 10 ml of concentrated hydrochloric acid, stirred and added at 70 C until no more bubbles were allowed to stand for 12 hours, filtered to give a yellow solid,The filter cake was washed with water and recrystallized from ethanol to give intermediate 4 as a yellow solid in 58.6% yield

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 30a E/Z-6-Chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one To the mixture of 6-chlorooxindole (16.2 g, 92 mmol) (Crescent) and 3-chlorobenzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) (Aldrich) dropwisely. The mixture was then heated at 70 C. for 3 hours. After cooling to 4 C., the resulting precipitate was collected and dried to give E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid. (Yield 25.2 g, 95%).

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; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in ‘solvent-free’ manner or with additive (‘on-solvent’ manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.

The synthetic route of 5-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E.; Arkivoc; vol. 2018; 4; (2018);,
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Electric Literature of 337536-15-9, 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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(a) To a solution of 4-bromoisoindolin-l-one (106 mg, 0.5 mmol) in acetonitrile were added K2C03(110 mg, 0.8 mmol) and ethyl 2-bromoacetate (52 muEpsilon, 0.5 mmol). The mixture was refluxed overnight. The solvent was evaporated off, and the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. Purification through flash chromatography on silica gel eluted with 8% menthol in methylene chloride gave ethyl 2-(4-bromo-l-oxoisoindolin-2-yl)acetate 150 mg as a brown gel, yield: 100%. LC/MS: (ESI) [M+H]+= 300.4

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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF WASHINGTON; FAN, Erkang; ZHANG, Zhongsheng; HUANG, Wenlin; BUCKNER, Frederick S.; (180 pag.)WO2018/237349; (2018); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 132898-96-5, 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. 132898-96-5 name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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.

Step 1: 5-(Pyrrolidin-1-ylsulfonyl)-1H-indole-2,3-dione To a cold solution of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (2.00 g, 8.14 mmol) in a 1:1 mixture of THF: CHCl3 (96 mL) was added drop-wise via syringe pump over a period of 1 hr a solution of pyrrolidine (0.885 mL, 10.6 mmol) and N, N-diisopropylethyl amine (2.84 mL, 16.3 mmol, 2 eq) in chloroform (16 mL) under a dry N2 atmosphere with cooling in an ice bath. After stirring for 1 h., the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 80/20 CH2Cl2/EtOAc to give the title compound as a greenish-yellow solid (0.88 g, 39% yield). NMR (300 Mz, DMSO-d6): consistent. MS: (ES-) m/z 279 [M-H].

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

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 552330-86-6, name is 5-Bromoisoindolin-1-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 552330-86-6, name: 5-Bromoisoindolin-1-one

(i) (S)-tert-Buty l-(l-amino-3-(4-(l-(difluoromethyl)-6-oxo-l,6-dihydropyridin-3- yl)phenyl)-l-oxopropan-2-ylcarbamoyl)cyclohexylcarbamatePotassium carbonate (178 mg) in water (5 mL) was added to (S)-tert-butyl l-(l-cyano-2-(4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)ethylcarbamoyl)cyclohexylcarbamate (Example 23 step (i), 300 mg), 5-bromoisoindolin-l-one (141 mg) and 1,1 bis(di-tert- butylphosphino)ferrocene palladium dichloride (12 mg) in degassed acetonitrile (15 mL) at 20C under an atmosphere of nitrogen. The resulting solution was stirred at 90C for 4h. The reaction mixture was concentrated to dryness and the residue purified by chromatography on silica eluting with ethyl acetate to afford the sub-titled compound (180 mg) as a colourless solid.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; KINCHIN, Elizabeth; MATHER, Andrew; METE, Antonio; MILLICHIP, Ian; STANIER, Andrew Geoffrey; WO2011/154677; (2011); A1;,
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Indoline | C8H9N – PubChem

Synthetic Route of 20780-72-7,Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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: In an ordinary vial equipped with a Teflon-coated stir bar, thiourea IV or V (0.04 mmol, 11.89 mg, 20 mol percent) was dissolved in 1.0 mL of THF. Then the corresponding isatins 1 (0.1 mmol, 1.0 equiv) was added, followed by the addition of alpha,beta-unsaturated ketones 2 (0.2 mmol, 2.0 equiv). The vial was capped with a rubber stopper and the mixture was stirred at room temperature for the time given in the tables. The crude mixture was then purified by flash column chromatography silica gel, using hexane/ethylacetate 2:1 as the eluent. Solvent was removed in vacuo to give the desired products.

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

Reference:
Article; Liu, Guo-Gui; Zhao, Hua; Lan, Yu-Bao; Wu, Bin; Huang, Xiao-Fei; Chen, Jian; Tao, Jing-Chao; Wang, Xing-Wang; Tetrahedron; vol. 68; 20; (2012); p. 3843 – 3850;,
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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., Formula: C9H6BrNO2

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

Reference of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of substituted isatins (1 mmol),cyclic 1,3-diketone (1 mmol), malononitrile (1 mmol)and nano Ag/kaolin (0.085 g, 7 mol%) in EtOH (10mL) was stirred at reflux temperature. Uponcompletion instead of compilation, monitored by TLC(n-hexane/ethyl acetate: 2/1), the reaction mixture wasallowed to cool to room temperature. The catalyst wasseparated by filtration of this solution. The solution wasconcentrated under vacuum to afford the product,which was purified by recrystallization in the ethanol.All the products were identified by comparing of meltingpoint and 1H NMR spectra with those of authenticsamples reported in the literature.

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

Reference:
Article; Sadeghi, Bahareh; Lasemi, Zahra; Azimi, Razieh; Oriental Journal of Chemistry; vol. 31; 2; (2015); p. 1175 – 1179;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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 334952-09-9, SDS of cas: 334952-09-9

Example 81 3-[4-(2-Diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid (80 mg, 0.45 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide to give 210 mg (92%) of the title compound as a yellow orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.6 (s, 1H, NH), 7.76 (d, J=8.0 Hz, 1H), 7.66 (s, 1H, H-vinyl), 7.57 (dd, J=1.5 & 8.0 Hz, 1H), 7.40-7.42 (m, 2H), 3.28 (m, 2H, CH2), 2.88 (m, H-piperidine), 2.54 (m, 6H, 3*CH2), 2.44 (s, 3H, CH3), 2.40 (s, 3H, CH3), 1.56 (m, H-piperidine), 0.97 (t, J=6.98 Hz, 6H, N(CH2CH3)2). MS m/z 424 [M+].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem