Month: April 2021

Related Products of 20870-79-5, A common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

General procedure: A reaction mixture of 5-nitroindolin-2-one (356 mg, 2 mmol),the appropriate aldehyde (2.4 mmol, 1.2 equiv.) and piperidine(21 muL, 0.2 mmol, 0.1 equiv) in DMF (5 mL) was stirred at 80 C for4 h. The solventwas removed under reduced pressure, the resultingresidue was suspended in ethyl ether (15 mL) and filtered, tofurnish the target compound used without any further purificationfor the next reaction.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romagnoli, Romeo; Baraldi, Pier Giovanni; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Salvador, Maria Kimatrai; Lopez-Cara, Luisa Carlota; Bortolozzi, Roberta; Mattiuzzo, Elena; Basso, Giuseppe; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 258 – 270;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6, 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 611-09-6 as follows.

General procedure: A mixture of malononitrile (1 mmol), isatin (1 mmol), dicarbonyl (1 mmol), PEGOSO3H(0.1 mmol), and water (2 mL) was stirred under reflux for the appropriate time (shown in Tables 3, 4). After completion of the reaction, the reaction mixture was filtered and the residue was washed with ethanol. The crude solid product was recrystallized from EtOH to afforded the pure products in high purity and yield.Assignment of the structures of the products was based on their 1H NMR, 13C NMR,and IR spectra.

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nasseri; Zakerinasab; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5261 – 5270;,
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. 3335-98-6, name is 1-Phenyloxindole, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H11NO

1-phenyl-2,3-dihydro-1H-indol-2-oneTo 100 g (0.48 mol) was added to 1.5 L CH2Cl2. It was added to phosphoryl chloride 267 mL (2.87mol) at room temperature and heated to reflux for 12 hours. Slowly added dropwise to the ice-water cooling, the reaction solution and the reaction was terminated. The organic layer was extracted with CH2Cl2 and 2.0 L sat. Neutralized with aqueous NaHCO3 solution and washed with distilled water. The resulting organic layer was dried over anhydrous MgSO4, and evaporated under reduced pressure and purified by silica gel column chromatography to give the title compound 40.3 g (yield 37%):

The synthetic route of 3335-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Doosan Corporation; Sim, Jae Uii; Park, Sung Jin; Jang, Ji Sung; (28 pag.)KR2016/41676; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

General procedure: An equivalent mixture of aldehyde (1 mmol) and active methylene compound- barbituric acid/1, 3-dimethyl barbituric acid/ 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1 mmol) in dimethyl formamide (2 mL) was subjected to microwave irradiations at 150 C for 1 h. The reaction was monitored by TLC. After the completion, the reaction was quenched by adding water to the reaction mixture. The crude product was separated out as solid, which was further purified by washing with ethanol, hot water and recrystallization from chloroform:methanol (9:1).

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Harpreet; Kaur, Manpreet; Kaur, Harpreet; Sharma, Indu; Bhandari, Anmol; Kaur, Gurcharan; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Chloroisoindoline-1,3-dione

7a: A mixture of concentrated sulfuric acid (24 mL) and fuming nitric acid (1.5 mL) was added dropwise to 4-chloro-phthalimide 6 (4.90 g, 27.0 mmol). The reaction mixture was heated at 80 C for 0.5 h. After cooling to r.t. the dark red solution was poured into ice. The resulted yellow precipitate was collected by filtration, washed with water, dried in vacuum affording a pale yellow solid 7a (3.52 g, 58% yield). 1H NMR (DMSO-d6): delta (ppm) 11.87 (s, 1H, CONHCO), 8.51 (s, 1H, Ar-H), 8.27 (s, 1H, Ar-H). 13C NMR (DMSO-d6): delta (ppm) 166.66, 166.62, 151.28, 135.96, 132.43, 130.30, 126.03, 119.62.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Xiaoyu; Zhao, Jing; Zhang, Wandong; Chen, Long; Chinese Chemical Letters; (2018); p. 331 – 335;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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 15362-40-0, Recommanded Product: 1-(2,6-Dichlorophenyl)-2-indolinone

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

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:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

56341-37-8, name is 6-Chlorooxindole, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 56341-37-8

General procedure: Synthesis of 6-chlorooxindole derivatives was carried out by refluxing 6-chlorooxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine. The reaction mixture was refluxed for 3 h. After completion of reactionas determined by TLC analysis, the contents were cooled and concentrated at reduced pressure to afford solid 3-oxindole derivatives. The product was washed with equal volumes of a mixture of hexane-ethyl acetate (25 mL) and dried to afford compounds 1-25.20 1H NMR, EI spectroscopy and CHN analysis were used for the determination of their structures. 4.1.18 (E)-3-(3-Methoxybenzylidene)-6-chloroindolin-2-one (18) Yield: 0.24 g (84%); 1H NMR (500 MHz, DMSO-d6): delta 10.75 (s, 1H, -NH), 7.63 (s, 1H, =CH), 7.52 (d, 1H, J4,5 = 8.0 Hz, H-4), 7.43 (t, 1H, J5′(4′,6′) = 8.0, H-5′), 7.24(t, 1H, J4′(3′,5′) = 8.0, H-4′), 7.23 (d, 1H, J6′,5′ = 8.0 Hz, H-6′), 7.04 (d, 1H, J3′,4′ = 8.0 Hz, H-3′), 6.93 (dd, 1H, J5,7 = 1.5, J5,4 = 8.0 Hz, H-5), 6.88 (d, 1H, J7,5 = 1.5 Hz, H-7), 3.79 (s, 3H, -OMe); MS: m/z (rel. abund.%) 285 (M+, 100), 178 (59), 152 (32), 63 (56); Anal. Calcd for C16H12ClNO2 (285.72): C, 67.26; H, 4.23; Cl, 12.41; N, 4.90; O, 11.20; Found: C, 67.28; H, 4.22; N, 4.88.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Momin; Yousaf, Muhammad; Wadood, Abdul; Junaid, Muhammad; Ashraf, Muhammad; Alam, Umber; Ali, Muhammad; Arshad, Muhammad; Hussain, Zahid; Khan, Khalid Mohammed; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3441 – 3448;,
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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Nitroindoline

Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h.The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine.The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-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 6941-75-9, Recommanded Product: 6941-75-9

Sodium borohydride (12.6 g, 330 mmol) was added to a mixed solvent of ethanol (300 mL) and water (50 mL)Add 5-bromophthalimide in 4 batches with stirring at 20-30 C(30.0 g, 132 mmol, stirred for 30 min after each addition).After the addition was complete, the reaction was incubated for 2h, hydrochloric acid solution (mass percent concentration 18%, 180g, 883.5mmol) was added dropwise at 20-30 C, heated to 75-85 C after dropping,The reaction was incubated 3h, evaporated to ethanol under reduced pressure to give an aqueous white solid.Solid plus toluene (225ml), water (300ml), 45-55 C for 30min, to clarify the upper and lower.The layers were separated and the aqueous layer was extracted with toluene (150 mL * 1).The combined toluene layers were washed with saturated brine (150 ml * 1).Divided toluene layer, add water 225ml, sodium hydroxide (6g), stirred at 80 for 3h. The hot toluene is removed by hot section and extracted with toluene (50 ml * 1).Sub-water layer was cooled to 30 C dropwise hydrochloric acid (21.0g), heated to 75-85 C, incubated for 2-3h.Drop to 50 C and extract with toluene (225 ml * 1, 150 ml * 1).Toluene was combined and washed with water (50 ml * 1).Atmospheric pressure concentrated toluene layer to 5.5X, slowly cooled to 50 precipitated white crystals, 50 stirring 1h, then slowly cooled to 0-5 incubated 1h.Filtration and crystallization from ice-toluene (60 ml) gave a white 5-bromophthalide (13.7 g, 48.5% yield) after drying in vacuo. HPLC: 98.0%.

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

Reference:
Patent; Shanghai He Quan Pharmaceutical Research And Development Co., Ltd.; Shanghai He Quan Pharmaceutical Co., Ltd.; Changzhou Hequan Pharmaceutical Co., Ltd.; Changzhou Hequan Drug Discovery Co., Ltd.; Guo Wei; Zhang Qing; Li Yongkai; Luo Qiyu; Xie Chengfu; Shi Feng; Fu Xiaoyong; Chen Minzhang; (7 pag.)CN107082769; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem