Author: Jessica.F

Application of 20780-72-7, 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 20780-72-7 as follows.

4-Bromoisatin 30 (1.00 g, 4.45 mmol), thiosemicarbazide (405 mg, 4.45 mmol) and K2CO3 (920 mg, 6.67 mmol) were suspended in water (50 mL). The reaction mixture was stirred at reflux for 16 h over which time the dark brown suspension became a clear light brown solution. The solution was carefully acidified by dropwise addition of acetic acid and resulting precipitate was filtered. The precipitate was recrystallised from DMF to yield the title compound (34) as a red solid (1.18 g, 95percent); mp (Gallenkamp) >300 °C; numax (solid) 3389 (br), 3297, 1604, 1573, 1140; deltaH (500 MHz, DMSO-d6, 363 K) 7.43-7.52 (3H, m, C(6)H, C(7)H), and C(8)H), 14.68 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 113.0, 117.0, 118.3, 127.4, 133.5, 136.1, 145.3, 149.9, 180.0; m/z (ESI-) 279 ([79BrM-H]-, 100percent), 281 ([81BrM-H]-, 100percent); HRMS (ESI-) C9H5BrN4S ([79BrM-H]-) requires: 278.9335; found 278.9343, ([81BrM-H]-) requires 280.9314; found 280.9320.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-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 7147-90-2, SDS of cas: 7147-90-2

General procedure: Phthalic anhydride or its derivatives (2.0 mmol) and 4-aminobutyric acid (2.0 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h. The reaction was quenched with water (10 mL) and was adjusted to pH 6-8 with NaOH (0.1 mol/L). The mixture was extracted with dichloromethane (10 mL × 3), and the organic layer was washed with aq. NaHCO3, and water and then evaporated to afford intermediate.

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

Reference:
Article; Wu, Hongna; Wu, Jun; Zhang, Wenxuan; Li, Zhongwen; Fang, Jinhui; Lian, Xu; Qin, Tong; Hao, Jie; Zhou, Qi; Wu, Song; Bioorganic and Medicinal Chemistry Letters; vol. 29; 7; (2019); p. 870 – 872;,
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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., Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A solution of isatins 1 (0.6 mmol), dienones 2 (0.4 mmol) and proline, thioproline or sarcosine(0.8 mmol) in the 10.0 mL of EtOH at reflux for 3 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc=5:1~3:1) were carried out to furnish the corresponding products 3-5.

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; Lin, Bing; Zhou, Gen; Gong, Yi; Wei, Qi-Di; Tian, Min-Yi; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Molecules; vol. 22; 4; (2017);,
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Synthetic Route of 2913-97-5, A common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

To a solution of Example 32A (12.1 g) in methanol (20 mL) was added L-isoleucine tert-butyl ester hydrochloride (13.0 g, 58 mmol), sodium cyanoborohydride (7.3 g, 116 mmol), and acetic acid (2 mL). The resulting solution was stirred for 3 hrs at 25° C. and the methanol removed under vacuum, dichloromethane (500 mL) added, and the solution extracted with aq. NaHCO3 (2.x.300 mL). Evaporation and purification of the organic layer gave 12.9 g of the title compound.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flentge, Charles A.; Chen, Hui-Ju; DeGoey, David A.; Flosi, William J.; Grampovnik, David J.; Huang, Peggy P.; Kempf, Dale J.; Klein, Larry L.; Krueger, Allan C.; Madigan, Darold L.; Randolph, John T.; Sun, Minghua; Yeung, Ming C.; Zhao, Chen; US2005/131042; (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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C22H19N3O6

The reaction flask was charged with 210.7 g (0.5 mol) of the compound prepared in Example 7,(S) -2- {[2-oxo-3- (4- (3-oxorpholine) phenyl) oxazolidin-5-yl] methyl} isoindole- VII),1500ml of anhydrous ethanol, 500ml of 30% aqueous solution of methylamine, stirring evenly,The temperature was raised to 40 C to 60 C for 8 hours,TLC in the control (dichloromethane: methanol = 20: 1, volume ratio) reaction is complete,With 10% hydrochloric acid to adjust the pH to 1-2 between the precipitation of a large number of white solid, cooling to about 15 C,Stirring for 2 hours, filtering, filter cake with 300ml anhydrous ethanol washing, vacuum drying,A mixture of 147.0 g of the white solid (compound of formula VIII) was obtained in a molar yield of 89.7%, and 1 ^ (purity: 98.7%).

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Li Linfeng; Zhang Zheng; Wang Wei; Ren Juan; (15 pag.)CN105085371; (2017); B;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-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 7699-18-5, COA of Formula: C9H9NO2

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

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; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, 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.

0.4 mmol of 4,7-dichloropurine, 0.2 mmol of antipyrine and 1 mL of water were mixed, and stirred under an oil bath at 100 C for 48 hours, and then the resulting reaction system was sequentially cooled to room temperature, filtered, washed with water and dried under vacuum ( 0.005 MPa, 80 C, 10 h) gave the title compound I-3 (yellow solid, yield 88%, purity 99.8%).

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
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Indoline | C8H9N – PubChem

Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

40 g of 7-fluoroanthraquinone was added to 450 ml of anhydrous methylene chloride, 15 g of aluminum trichloride was added, 60 g of oxalyl chloride was added, the mixture was heated to reflux for 2 hours, cooled to room temperature, and then water was added thereto for liquid separation, drying, and concentration. The residue was columned to give 47 g of 2-(7-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Cheng Jia; (6 pag.)CN107698483; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

A solution of 4-bromoisoindoline hydrochloride (8.00 g, 34.33 mmol) in dichloromethane (20 mL) and triethylamine (14.3 mL, 103.0 mmol) was cooled to 0 C, and then di-tert-butyl dicarbonate (15.0 g, 68.73 mmol) was added. The mixture stirred overnight at room temperature and was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of dichloromethane, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 :5)) to afford tert-butyl 4-bromoisoindoline-2-carboxylate (9 g, 75%) as a white solid. MS: (ESI, m/z): 242 [M-t-Bu+H]+

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 32372-82-0, 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. 32372-82-0, name is Isoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (5.20 g, 27.64 mmol, 2 eq.) was added to a stirred solution of 83 (3.0 g, 13.82 mmol, 1 eq.), isoindoline hydrochloride (3.22 g, 20.73 mmol, 1.5 eq.), 1- hydroxybenzotriazole (3.73 g, 27.64 mmol, 2 eq.) N,N-diisopropylethylamine (4.81 mL, 27.64 mmol, 2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 84 (3.24 g,77.9 %) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.92 (s, 1H), 7.73 (d, J= 2.2 Hz, 1H), 7.48 (dd, J= 8.8, 2.4 Hz, 1H), 7.34 (s, 4H), 6.94 (d, J= 8.8 Hz, 1H), 5.10 (s, 4H).13C NMR (100MHz, CDCI3) delta 169.4, 159.4, 136.1 (2), 134.8, 130.5, 128.2 (2), 122.8 (2), 120.2, 118.7 110.2, 55.8, 53.3. HRMS (ESI+) m/z [M + H+] calcd for C15H13BrN02, 318.0130, found 318.0119.

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, Isoindoline hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem