Month: August 2021

Application of 603-62-3, 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 603-62-3 as follows.

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Muller, George W.; Schafer, Peter H.; Man, Hon-Wah; Zhang, Ling-Hua; Gandhi, Anita; Chopra, Rajesh; US2012/230983; (2012); A1;,
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Related Products of 21857-45-4, A common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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 100 mL round- bottomed flask, flushed with nitrogen, were added 17 (91 mg, 0.5 mmol), 5-methoxyindoline (82 mg, 0.55 mmol), BuOH (10 mL), and 2-3 drops of cone. HC1. The reaction mixture was heated at reflux with stirring for 12 h until the starting material 17 disappeared (TLC). The reaction solution was allowed to cool to room temperature; the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel with hexane: acetyl acetate = 20: 1 as the eluent. Fractions containing the product (TLC) were combined and evaporated to afford 93 mg (63%) 8 as a white powder: mp 201.1-202.3 C; Rf 0.5 (AcOEt/Hexane 3 : 1); 1H NMR (DMSO-d6) delta 2.42 (s, 3 H), 2.53 (s, 3 H), 3.25 (t, 2 H), 3.75 (s, 3 H), 4.39 (t, 2 H), 6.79 (t, 2 H), 6.89 (d, 1 H), 8.48 (d, 1 H), Anal. Ci7H17N302

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; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (111 pag.)WO2016/100495; (2016); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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 1035235-27-8, SDS of cas: 1035235-27-8

Carbon dioxide (g, 60 atm) was introduced into a lOO-mL pressure tank reactor containing a solution of tert-butyl 4-bromo-2,3-dihydro-lH-isoindole-2-carboxylate (2.00 g, 6.71 mmol), triethylamine (2.80 mL, 20.1 mmol), and [l,l?-bis(diphenylphosphino)ferrocene]- dichloropalladium (II), complex with dichloromethane (820 mg, 1.12 mmol) in ethanol (50 mL). The resulting mixture stirred overnight at 120 C. The reaction was concentrated under vacuum and then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate, washed with 100 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 : 10)) to afford 2-(tert-butyl) 4-ethyl isoindoline-2,4-dicarboxylate (1.67 g, 85%) as an off-white solid. MS: (ESI, m/z): 292[M+H]+

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:
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

Application of 550-44-7, A common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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 suspension of LiAlH4 (1.1403 g) in dry THF (24 ml) under argonatmosphere, a solution of MeOH (2 ml) in THF (24 ml) was added over 16 min at 0C,followed by cooling of the whole to -74C (in an acetone-dry ice bath). To thissuspension, N-methylphthalimide 13 (1.6177 g, 10.0 mmol) was added in portions at-74C, and the mixture was stirred at this temperature for 40 min. Then the mixture was stirred at 0C for 45 min. A saturated aqueous solution of sodium sulfate (8 ml) wasadded, and the resultant inorganic salt was filtered by suction, and the precipitate waswashed with acetone. The combined organic layer was dried over magnesium sulfate,and the organic solvent was evaporated at 30C to give the residue 14 (yellow solid,1.1544 g, 88% yield). This intermediate is rather unstable, and it was used with furtherpurification. 1H-NMR (CDCl3): delta = 7.500 (2H, m), 7.040 (2H, s), 6.904 (2H, m), 3.987(3H, s).

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kozai, Daisuke; Kabasawa, Yoji; Ebert, Maximilian; Kiyonaka, Shigeki; Firman; Otani, Yuko; Numata, Tomohiro; Takahashi, Nobuaki; Mori, Yasuo; Ohwada, Tomohiko; Molecular Pharmacology; vol. 85; 1; (2014); p. 175 – 185;,
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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 1168150-46-6

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. name: 5-Bromoisoindoline-1,3-dione

5-Bromophthalimide (1.76 g, 7.8 mmol) was dissolved in abs. ethanol (75 ml), the mixture was heated to 60 C. and an aqueous solution of potassium hydroxide (4 ml, 10.5 mmol) was added dropwise. After 30 min of stirring at 60 C., the reaction mixture was cooled quickly with the aid of an ice bath, and the resulting precipitated colourless solid was filtered off with suction, washed with cold ethanol and dried under reduced pressure. In this manner, potassium 5-bromophthalimidate (1.04 g, 50% of theory) were obtained in the form of a colourless solid. 1H-NMR (400 MHz, d6-DMSO delta, ppm) 7.59 (dd, 1H), 7.45 (d, 1H), 7.29 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GmbH; Frackenpohl, Jens; Zeiss, Hans-Joachim; Heinemann, Ines; Willms, Lothar; Mueller, Thomas; Busch, Marco; Von Koskull-Doeering, Pascal; Rosinger, Christopher Hugh; Dittgen, Jan; Hills, Martin Jeffrey; US2014/302987; (2014); A1;,
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Application of 611-09-6, A common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 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.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasseri; Zakerinasab; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5261 – 5270;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-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.

Example 51 5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)amide 5-Bromo-1,3-dihydroindol-2-one (0.17 g, 0.8 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (0.2 g) to give 0.09 g (26%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.61 (s, br, 1H, NH), 10.98 (, br, 1H, NH), 8.09 (d, J=1.7 Hz, 1H, H-4), 7.76 (s, 1H, H-vinyl), 7.42 (t, J=5.5 Hz, 1H, CONHCH2), 7.24 (dd, J=1.7 & 8.0 Hz, 1H, H-6), 6.82 (d, J=8.0 Hz, 1H, H-7), 3.23-3.32 (m, 2H, NCH2), 2.46-2.55 (m, 6H, 3*NCH2), 2.43 (s, 3H, CH3), 2.42 (s, 3H, CH3), 0.96 (t, J=7.2 Hz, 6H, 2*NCH2CH3). MS-EI m/z 458 and 460 [M+-1 and M++1].

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
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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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

N-phenyl-2-indolone (1a, 0.3 mmol), t-butyl nitrite (t-BuONO, 2a, 1.2 mmol) and water (2 mL) were added to 10 mL of Schlenk vials and the reactor 25 C under stirring conditions, The reaction was monitored by TLC or GC until the reaction with N-phenyl-2-indolone was complete and the reaction was stopped. The reaction was diluted with ethyl acetate, The organic phase was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure. The residue was separated by column chromatography (n-hexane / ethyl acetate). The organic phase was extracted with ethyl acetate and the organic phase was separated. Ester) to give the desired product N-phenyl-isato-3-oxime I-3, yield 89%

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 3335-98-6.

Reference:
Patent; Ningbo University; Wu Yi; Wei Wenting; Zhu Wenming; Huang Yiling; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107162951; (2017); A;,
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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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H8BrNO3

To a clean dry flask containing suspension of 2-(2-bromoethoxy)isoindoline- l,3-dione (30 g, 0.111 mol), 1H- 1,2,3 triazole (7.66 g, 111 mmol) in dimethylformamide (150 ml) was added cesium carbonate ((36 g, 111 mmol) portion wise at room temperature under stirring. After 17 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (1050 ml) under stirring. After 30 minutes of stirring, the separated precipitates were collected by filtration and washed with water (100 ml). The collected precipitates were dried at 40 C for 2 hours under high vacuum to obtain 18.5 g of a mixture of 2-[2-(2H- l,2,3-triazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2- (lH- l,2,3-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as a white compound in 65% yield. Analysis: Mass: 259.2 (M+l); for Molecular weight: 258 and Molecular formula: C12H10N4O3; To a solution of mixture of 2-(2-(2H-l,2,3-triazol-2- yl)ethoxy)isoindoline-l,3-dione and 2-(2-(lH-l,2,3-triazol-l-yl)ethoxy)isoindoline-l,3-dione (13 g, 50.3 mmol, obtained from Step 1) in dichloromethane (130 ml) was added hydrazine hydrate (3.7 ml, 75.7 mmol) under stirring at room temperature. After 2 hours, the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol as solvent system. After completion of the reaction the unwanted solid was filtered out and washed with dichloromethane (25 ml). The collective filtrates were concentrated at 40 C under high vacuum to dryness to provide 6.5 g of a mixture of 2-[2-(aminooxy)ethyl]-2H-l,2,3-triazole and l-[2- (aminooxy)ethyl]-lH-l,2,3-triazole, which was used as such in the next step without any further purification

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 5181-35-1.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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