Tag: M.W=100-200

39755-95-8, 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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of acetophenone or isatin (5 mmol) in THF (10 mL), BF3¡¤OEt2 (7.5 mmol) was added at 0C under the atmosphere of N2 and the mixture was stirred for 10 minutes. To the cooled mixture, anhydrous hydrazine (7.5 mmol) was added in one portion and the reaction mixture was stirred at 0C under the atmosphere of N2 for 30 min. The reaction was quenched by the addition of a saturated solution of NH4Cl (4 mL), extracted by ethyl acetate (3 ¡Á 15 mL) and purified by column chromatography (ethyl acetate-CH2Cl2; 3 : 7) to afford hydrazones 2-22.

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; El-Azab; Ghabbour; El-Husseiny; Maarouf; Mohamed; Abdel-Aziz; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2837 – 2844; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2837 – 2844,8;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 324-03-8, name is 6-Fluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 324-03-8

General Procedure: To a solution of 4-chloro isatin (500 mg, 2.75 mmol) in acetone (5 mL) was added diethylamine (314 muL, 3.02 mmol) at room temperature. The mixture was heated to 50 oC for 14 hours with magnetic stirring and then concentrated under reduced pressure. The resulting alcohol intermediate was triturated in diethyl ether with sonication, filtered and the resulting white solids were used without further purification. To a solution of the alcohol intermediate dissolved in ethanol (3 mL) was added concentrated hydrochloric acid (1 mL). The mixture was stirred at room temperature for 14 hours and then quenched with a solution of saturated sodium bicarbonate (5 mL). The mixture was extracted with dichloromethane (20 mL), concentrated and purified by silica gel flash chromatography using a gradient of 30 – 80% ethyl acetate in hexanes to afford the target compound 10 as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 324-03-8. I believe this compound will play a more active role in future production and life.

Reference:
Conference Paper; Kloeck, Cornelius; Jin, Xi; Choi, Kihang; Khosla, Chaitan; Madrid, Peter B.; Spencer, Andrew; Raimundo, Brian C.; Boardman, Paul; Lanza, Guido; Griffin, John H.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 9; (2011); p. 2692 – 2696;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

(b) Preparation of 5-Nitro-2-oxindole. The 2-oxindole (6.5 g) was dissolved in 25 mL of concentrated sulfuric acid and the mixture maintained at -10-15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice water. The precipitate was collected by filtration, washed with water and crystallized from 50% of the acetic acid. The final crystal was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

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

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is Indolin-2-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. 59-48-3

To a solution of indolin-2-one (5 g, 37.55 mmol) and LiCl (5.6 g, 131.4 mmol) in THF (100 mL) was added w-BuLi (2.5 M, 30 mL) at -78 ¡ãC. The mixture was stirred at -78 ¡ãC for 20 min, followed by the addition of Mel (4.8 mL, 75.1 mmol). The reaction was stirred at 25 ¡ãC overnight, then quenched with saturated aqueous NH4C1 (100 mL) and diluted with EtOAc (100 mL x 3). The organic phase was washed with H20 (100 mL) followed by brine (100 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silca gel column chromatography (PE/EtOAc (v/v) = 8/1) to give the title compound as a white solid (2.92 g, 48.3percent). MS (ESI, pos. ion) m/z: 162 [M + H]+; NMR (CDCI3) delta (ppm): 9.23 (s, 1H), 7.21-7.18 (m, 2H), 7.04 (t, 1H), 6.96 (d, 1H), 1.41 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59-48-3.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 603-62-3, name is 3-Nitrophthalimide, 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 603-62-3. 603-62-3

Thiosalicylic acid (15.4 g, 0.1 mol) in NaOH aqueous solution (200 mL, 1 mol/L) was warmed until the solid dissolved, and then continually warmed to remove water. Ethanol was added into the sticky mixture, and then the white precipitates were collected by filtration, washed with ethanol, and dried in vacuo to obtain sodium thiosalicylate (f). A mixture of f (18.215 g, 0.1034 mol), 3-nitrophthalimide (15.892 g, 0.0827 mol), and DMF (200 mL) was stirred at 80 C for 8 h. A HCl solution (200 mL, 2 mol/L) was added. The precipitate was filtered, washed with water, dried in vacuo, and then recrystallized from dioxane to give a yellow powder. Yield: 95.4%. 1H NMR (300 MHz, DMSO-d6): delta 7.29-7.31 (m, 2H), 7.47 (m, 2H), 7.66 (m, 2H), 7.86 (m, 1H). Anal. Calcd. for C15H9NO4S: C, 60.19; H, 3.03; N, 4.68; S, 10.71; Found: C, 59.48; H, 3.20; N, 4.54; S, 10.51.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Nitrophthalimide.

Reference:
Article; He, Ming-Hui; Xu, Rui-Xin; Chen, Guang-Xue; Zeng, Zhao-Hua; Yang, Jian-Wen; Chinese Chemical Letters; vol. 25; 11; (2014); p. 1445 – 1448;,
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. 2058-74-4, name is 1-Methylisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 2058-74-4

General procedure: A solution of N-methylisatin (81 mg, 0.5 mmol), phenylacethylene (77 mg, 0.75 mmol), CuI (19 mg, 0.1 mmol), and Cs2CO3 (245 mg, 0.75 mmol) in CH3CN (1.0 mL) was stirred at room temperature for 18 h. After aqueous extractive work up and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 81 mg (61%). Other compounds were prepared similarly, and the spectroscopic data of unknown compounds 1b, 1d, and 1e are as follows.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roh, Hwa Jung; Lim, Jin Woo; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 57; 38; (2016); p. 4280 – 4283;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, 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 324-03-8 as follows.

To a 250 mL round-bottom flask was added 6-fluoro-2,3-dihydro-lH-indole-2,3-dione (8 g, 48.45 mmol, 1.0 equiv.), iodomethane (15.1 g, 106.38 mmol, 2.2 equiv.), potassium carbonate (26.7 g, 193.18 mmol, 4.0 equiv.), and CH3CN ( 150 mL). The resulting mixture was stirred overnight at 60 C. The reaction was quenched with water. The resulting solution was extracted with ethyl acetate (100 mL x 3); and the combined organic layers were washed with brine (50 mL x 2), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified via silica gel column chromatography eluting with ethyl acetate/petroleum ether (20%-40%) to give 6-fluoro-l-methyl-2,3-dihydro-lH-indole-2,3-dione 30b (7 g, 81%) as a red solid.

According to the analysis of related databases, 6-Fluoroindoline-2,3-dione, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

222036-66-0, The chemical industry reduces the impact on the environment during synthesis 222036-66-0, name is 5-Aminoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

To a solution of 5-aminoisoindolin-1-one (2.96 g, 20 mmol) in chloroform (50 mL) was added N-chlorosuccinimide (2.67 g, 20 mmol), and stirred under reflux for 2 hours. The resulting mixture was evaporated, concerntrated and then purified by silica gel column chromatography to give 4-chloro-5-aminoisoindolin-1-one (2.58 g). Yield: 70percent. MS m/z[ESI]: 183.0[M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Aminoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, 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 496-12-8 as follows.

2) Triethylamine (0.33 ml, 2.37 mmol) and isoindoline (0.27 ml, 2.38 mmol) were added in turn to a solution of methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (820 mg, 2.25 mmol) in dimethyl sulfoxide (5 ml) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and ice water (50 ml) was added thereto. The mixture was stirred and the precipitates were filtered, washed with water and dried. The resultant yellow crystals were purified by column chromatography on silica gel (n-hexane/ethyl acetate=15) to give methyl ester of 5-chloro-2-(1,2,3,4-tetrahydroisoquinolinio)-3-nitrobenzoic acid (608 mg, 81%) as yellow crystals. m.p.: 114-115 C.; IR (Nujol) : 1743, 1705, 1603, 1589, 1529, 1503 cm-1; APCI-MS m/z: 333[M+H]+.

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

Reference:
Patent; J-Pharma Co., Ltd.; ENDOU, Hitoshi; WEMPE, Michael F.; PEYRON, Jean-Francois; ANZAI, Naohiko; JUTABHA, Promsuk; (83 pag.)EP2959918; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, 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.

General procedure: Acetone (150mL) and dibromoalkyl (30mol) were added to a 250mL three-necked round-bottom flask fitted with a mechanical stirrer and reflux condenser. Potassium phthalimide (11.85g, 10 mol) was added slowly over a 15-min period, and then the reaction mixture was heated under reflux for 10h. The reaction mixture was filtered via suction, and the acetone was removed via rotary evaporation. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:14) to afford 2-5 as white solid.

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; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem