Category: indolines-derivatives

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 7699-18-5 as follows. Computed Properties of C9H9NO2

General procedure: Compounds 8 and 10 were prepared from azo coupling of aryldiazonium salts 3a,b with5-methoxyindolin-2-one 2, previously described [24]. Aryldiazonium salts were prepared startingto corresponding amines (21.5 mmol) in HCl 6N (11 mL) with water solution (7.5 mL) of sodiumnitrite (23 mmol). This solution was added to solution of indol-2-one (21.5 mmol) and sodium acetate(43 mmol) in methanol (59 mL) at 0 C. The resulting precipitate was filtered and purified.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco; Molecules; vol. 23; 7; (2018);,
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Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

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

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
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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. 20870-79-5, name is 5-Nitroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6N2O3

5-Nitro-1,3-dihydro-indol-2-one 30b (3.56 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) to the solution at room temperature. The reaction mixture was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 5-amino-1,3-dihydro-indol-2-one 30c (2.04 g, yield 68.9%) as a white solid. MS m/z (ESI): 149.4[M+1]

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

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
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Application of 39755-95-8, The chemical industry reduces the impact on the environment during synthesis 39755-95-8, name is 5-Methoxyisatin, I believe this compound will play a more active role in future production and life.

The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflux for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 1.1 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrazinocarbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid.

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, 5-Methoxyisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
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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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 6-Bromoisatin

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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 6326-79-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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Application of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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.

In a 10 mL flask 94 mg (0.58 mmol) 2 and 171 mg (0.64 mmol) 3 [24] were dissolved in 3.0 mL of ethyl alcohol, four drops of piperidine were added and the mixture was refluxed for 4 h. The solution was allowed to cool and stored in a refrigerator overnight. The orange crystals that have precipitated were filtered andwashed with small amounts of ethyl alcohol and petrol ether and yielded after drying under vacuum 107 mg (45%) of 5. Mp: 220e222 C, 1H NMR (d, ppm, DMSO-d6): 0.99 (t, 6H, 2 CH3), 2.45 (s, 3H, CH3/ pyrrole), 2.46 (s, 3H, CH3/pyrrole), 2.52 (m, 6H, 3 CH2), 3.29 (q, 2H, CH2), 3.79 (s, 3H, CH3O), 6.71 (m, 1H, CH), 6.78 (d, 1H, CH), 7.42 (t, 1H, CONH), 7.50 (d, 1H, CH), 7.68 (s, 1H, CHvinyl), 10.72 (s, 1H, NHoxindole), 13.76 (s, 1H, NHpyrrole), 13C NMR (d, ppm, DMSO-d6): 10.63 (CH3), 11.84 (CH3), 13.23 (CH3), 36.90 (CH2), 46.43 (CH2), 51.56 (CH2), 55.56 (OCH3), 104.44, 109.80, 112.54, 115.60, 120.27, 13.64, 125.62, 126.40, 129.00, 132.19, 135.65, 154.81 (12 C]C), 164.52 (C]O), 169.42 (C]O), ESI-MS (ESth): m/z ¼ 411.42 (M th H).

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Caballero, Julio; Munoz, Camila; Alzate-Morales, Jans H.; Cunha, Susana; Gano, Lurdes; Bergmann, Ralf; Steinbach, Joerg; Kniess, Torsten; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 272 – 280;,
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Related Products of 24566-79-8, These common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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 mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL × 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

Statistics shows that N-(6-Bromohexyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 24566-79-8.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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Related Products of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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: Indoles 1 (0.5 mmol), DMSO (3mL) and I2O5 (1 mmol) were added into a flask and vigorously stirred at 80oC under air. The reaction was stopped until indoles were completely consumed as monitored by TLC analysis. After the completion of reaction, saturated Na2S2O3 solution (20 mL) was added to the mixture. The mixture was extracted with EtOAc (3×20 mL) and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. Then, the crude product was purified by column chromatography on silica gel using ethyl acetate and petroleum ether as the eluent to give the products 2.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ci-Ping; Jiang, Guo-Fang; Tetrahedron Letters; vol. 58; 18; (2017); p. 1747 – 1750;,
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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., COA of Formula: C9H9NO

General procedure: Equimolar quantity of 5-substituted-1H-indolin-2-ones and 2-(4-formylphenoxy)-N-substituted-phenyl-acetamide was taken into round bottom flask containing 50 mL of methanol, followed by 2-3 drops of piperidine. The reaction mixture was refluxed for 1-4 h or till the end of reaction as confirmed by TLC. Then, it was cooled to room temperature and, the solution was filtered. The obtained residue was recrystallized by using dimethylformamide and 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; Bhadauria, Vivek Singh; Sravanthi, Vishnu; Kumar, Sujeet; Das, Debajyoti; De Clercq, Erik; Schols, Dominique; Tokuda, Harukuni; Karki, Subhas S.; Acta poloniae pharmaceutica; vol. 74; 1; (2017); p. 137 – 145;,
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Synthetic Route of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

Example 1 (3Z)-3-[(4-{[2-(diethylamino)ethyl]carbamoyl}-3,5-dimethyl-1H-pyrrol-2-yl)methylene]-2-oxoindoline-5-carboxylic acid (1) A mixture of 2-oxoindoline-5-carboxylic acid (0.708 g, 4 mmol), 3,5-dimethyl-4-(piperidin-1-ylcarbonyl)-1H-pyrrole-2-carbaldehyde (1.030 g, 4.4 mmol) and piperidine (0.2 mL) in EtOH (75 mL) was refluxed for 8 h. The mixture was cooled down to room temperature to provide a precipitate which was filtered and washed with EtOH to provide the target compound 1 (0.980 g, 62.25%) NMR (300 MHz, DMSO-d6) delta ppm: 13.52 (s,1H), 12.5 (bs,1H), 11.19 (s,1H), 8.37 (s,1H), 7.78 (s,1H), 7.77 (d,1H), 6.96 (d,1H), 3.43 (m,4H), 2.29 (s,6H), 1.60 (bs,2H), 1.47 (bs,4H); tR: 3.18 min, MS (ESI): m/z (M+H)+ 394; (M+H)-392.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; Oerfi, Zoltan; EP2837626; (2015); A1;,
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