Month: January 2021

Application of 3676-85-5, 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

10 parts of 4-aminophthalimide and 11 parts of cyanuric chloride were added to 100 parts of nitrobenzene, and the mixture was heated at 100 to 110 C. for 5 hours. After cooling it was filtered and washed with methanol and water. And dried at 80 C. to obtain 17 parts of the intermediate (2) represented by the formula (2).

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

Reference:
Patent; Dainichiseika Color & Chemicals Mfg. Co., Ltd.; Iguchi, Kazunori; Yanagimoto, Hiromitsu; (18 pag.)JP5823432; (2015); B2;,
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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. 3484-35-3, name is 5-Methylindolin-2-one, A new synthetic method of this compound is introduced below., name: 5-Methylindolin-2-one

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3¡¤Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

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; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
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Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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.

Description 12:(Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-5-methoxyindolin-2-one5-Methoxyindolin-2-one (50 mg, 0.31 mmol) and 3,5-dimethyl-W-pyrrole-2- carboxaldehyde (1.2 equiv., 45 mg) were heated together in ethanol (1 ml) and piperidine (2 drops) in a microwave (150C, 30 min). The reaction mixture was cooled to room temperature and diluted with ethanol. The precipitate was filtered, washed with ethanol, and then with ethyl ether, air-dried to give the product as an orange crystalline solid. The results set out below indicate the final product was the title compound 012.1H NMR (dmso-d6): 13.45 (1H, NH, br s), 10.58 (1H, NH, br s), 7.57 (1H, s), 7.40 (1H, s), 6.75 (1H, d), 6.65 (2H, d), 6.00 (1H, s), 3.77 (3H, s), 2.31 (6H, s).13C NMR (CDC ): 169.9, 155.5, 137.0, 32.7, 131.0, 127.6, 127.0, 123.6, 112.7, 112.0, 111.2, 109.5, 103.7, 56.0, 13.9, 11.7.MS: MH+ 269.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxyindolin-2-one, its application will become more common.

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, category: indolines-derivatives

Step 10b, Example 25b: (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one In a 25 ml round-bottomed flask, 71 mg of the sodium salt of [4-(2-hydroxymethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 25b, step 9b) and 38 mg of 4-chloro-2,3-dihydro-1H-indole are placed in 1 ml of dimethylformamide and 0.24 ml of pyridine, and then 57 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added. The reaction medium is stirred at ambient temperature for 20 h, then evaporated, water is added, and the resulting mixture is triturated. The solid formed is filtered off, and rinsed successively with water then with diisopropyl ether, with methylene chloride and then with pentane. The resulting solid is dried under vacuum for 2 h. (-)-2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-hydroxymethylmorpholin-4-yl)-3H-pyrimidin-4-one (62 mg) is isolated in the form of a pulverulent solid (yield=63%).Mass Spectrometry:The spectra were obtained on a Waters UPLC-SQD apparatusIonization: positive and/or negative mode electrospray (ES+/-)Chromatographic Conditions: Column: Acquity BEH C18-1.7 mum-2.1¡Á50 mm Solvents: A: H2O (0.1% formic acid) B: CH3CN (0.1% formic acid) Column temperature: 50 C. Flow rate: 1 ml/min Gradient (2 min): from 5 to 50% of B in 0.8 min; 1.2 min: 100% of B; 1.85 min: 100% of B; 1.95: 5% of BAnalytical Results:Retention time Tr (min)=0.66; [M+H]+: m/z 405; [M-H]-: m/z 4031H NMR spectrum (400 MHz): 2.58 (partially masked m, 1H); 2.83 (m, 1H); 3.19 (t, J=8.7 Hz, 2H); 3.27 to 3.52 (partially masked m, 4H); 3.77 (s, 2H); 3.82 to 3.96 (m, 2H); 4.12 (m, 1H); 4.21 (t, J=8.7 Hz, 2H); 4.71 (t, J=6.1 Hz, 1H); 5.20 (s, 1H); 7.09 (d, J=7.9 Hz, 1H); 7.22 (t, J=7.9 Hz, 1H); 7.97 (d, J=7.9 Hz, 1H); 11.61 (broad s, 1H)Optical rotation: alphaD=-22 C.=0.351 mg/0.5 ml in DMSO

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
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Related Products of 18711-13-2, 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 18711-13-2 as follows.

In these schemes, ketone (4.0 equv.) and a catalytic amount of diethylamine (10 drops) are added to a solution of substituted isatin (1.0 equv.) in methanol (5 mL). The mixture is stirred at room temperature until starting material (substituted isatin) disappears completely. The resulting solution is concentrated and applied to flash chromatography eluting with hexane / ethyl acetate to afford pure product in quantitative yield. Further purification is done by recrystallization with hexane / ethyl acetate.; 4,7-Dichloro-3-[2-(4-chlorophenyl-2-oxoethyl)]-3-hydroxyI-l,3-dihydroindol-2-one (YK-4-275): white solid; mp 194-196 0C; 1H NMR (DMSO, 400 MHz) delta 10.96 (s, IH), 7.93 (d, 2H, J = 8.8 Hz), 7.57 (d, 2H, J = 8.8 Hz), 7.30 (d, IH, J = 8.8 Hz), 6.90 (d, IH5 J = 8.8 Hz), 6.47 (s, IH), 4.36 (d, IH, J= 18.4 Hz), 3.71 (d, IH5 J= 18.0 Hz).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGETOWN UNIVERSITY; WO2008/83326; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-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. COA of Formula: C9H6ClNO2

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 mol%) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

The synthetic route of 5-Chloro-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, A new synthetic method of this compound is introduced below., Product Details of 675109-45-2

To a toluene solution (5 mL) of compound Int-1 (100 mg), m-CPBA (146 mg) was added and stirred at room temperature overnight to obtain a solution A. NaH (56 mg) was added to a DMF (5 mL) solution in which Compound A-31 (54 mg) was dissolved, and stirred at room temperature for 30 minutes to obtain a mixture B. Then A was slowly added to B and stirred overnight at room temperature. The reaction solution was poured into a saturated ammonium chloride solution, a white solid was precipitated, and the filter cake was purified by thin layer chromatography TLC (dichloromethane: methanol (v / v) = 20: 1) to obtain a crude product. Methanol (2 mL) was added, and then placed in an ultrasonic cleaner for 5 minutes, filtered, and the filter cake was dried to obtain the standard product HY-B030 (5.8 mg) as a 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:
Patent; Shanghai Hongyi Biological Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Wu Rongguang; Li Jia; Yi Dewu; Zhou Yubo; Ye Wei; Wang Peipei; Xiang Junfeng; Zhang Kaixiang; Hu Xiaobei; (61 pag.)CN110872296; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3485-84-5, 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. 3485-84-5, name is N-Vinylphthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Using N-vinylphthalimide and diphenylphosphine oxide as raw materials, the reaction steps are as follows:Add N-vinylphthalimide (0.069 g, 0.4 mmol) to the reaction flask.Phosphorus phenoxide (0.242 g, 1.2 mmol), trimethylsilyl isothiocyanate (0.157 g, 1.2 mmol), CuBr2 (0.009 g, 0.04 mmol), bipyridyl (0.006 g, 0.04 mmol), manganese acetate (0.322 g, 1.2 mmol) and N-methylpyrrolidone (5 mL), reacted at room temperature;TLC tracks the reaction until it is completely over;The crude product obtained after the reaction is completed is separated by column chromatography (ethyl acetate:dichloromethane = 1:10).The target product was obtained (yield 78%).

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, N-Vinylphthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Soochow University (Suzhou); Zou Jianping; Tao Zekun; Zhang Peizhi; Li Jianan; (19 pag.)CN107556340; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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. Recommanded Product: 2913-97-5

Compound 2: NaBH(OAc)3 (3,05 g ;14,4 mmol) was added to a solution of N- ethylaniline (1,16 g ; 9,6 mmol) and 2-phthalimidoacetaldehyde (1) (2,72 g, 14,4 mmol) in CH2C12 (28 mL). After 24 h at 20¡ãC, CH2C12 was added and the organic phase was washed with H20, dried (MgS04) and evaporated. The crude product was purified by chromatography over silica gel (80:20 CH2Cl2-cyclohexane) to afford 2 as a yellow solid (2,71 g, 96 percent). 1H NMR (250 MHz, CDC13): delta 7,85 (m, 2H), 7,71 (m, 2H), 7.24 (t, J = 7,8 Hz, 2H), 6,86 (d, J = 7,8 Hz, 2H), 6.67 (t, J = 7,8 Hz, 1H), 3.91 (dd, J = 6,5, 8,1 Hz, 2H), 3,58 (dd, J = 6,5, 8,1 Hz, 2H), 3,46 (q, J = 6,9 Hz, 2H), 1.22 (t, J = 7,0 Hz, 3H). 13C NMR (63 MHz, CDC13): <5 168,0 (C), 147,2 (C), 133,7 (CH), 131 ,8 (C), 129,2 (CH), 123,0 (CH), 116,0 (CH), 111,9 (CH), 47,8 (CH2), 44,6 (CH2), 35,0 (CH2), 12,2 (CH3). MS: m/z = 295 (MH+). Anal, calcd for Ci8Hi8N202 (294,14), C 73.45, H 6,16, N 9,52. Found C 73,33, H 6,17, N 9,62. The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; UNIVERSITE PARIS DESCARTES; SLAMA-SCHWOK, Anny; BOUCHER, Jean-Luc; XU-LI, Yun; DEPREZ, Eric; HENRY, Etienne; DESSY, Chantal; FERON, Olivier; TARUS, Bogdan; WO2012/175516; (2012); A1;,
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