Author: Jessica.F

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;,
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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. 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;,
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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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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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Electric Literature of 446292-08-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 446292-08-6 name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

25 g (0.012 mol) of 2-({(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1 ,3-oxazolidin- 5-yl}methyl)-1 H-isoindole-1 ,3(2H)-dione (II), 1 1.2 mL of methylamine (40% aqueous solution, 0.058 mol) and 125 mL of methanol were charged in a 500 mL flask. Then, the reaction mass was heated to reflux for 1 hour and concentrated under reduced pressure. The crude product was slurried in 125 mL of toluene and 16.5 mL of triethylamine were added to the reaction mass at 25 C. Afterwards, 17.81 g (0.098 mol) of 5-chlorothiophene-2-carbonyl chloride in 100 mL of toluene were added dropwise and the reaction mass was stirred for 1 hour at 25 C. At this stage, the reaction mass was heated at 50 C for 1 hour and 75 ml of water was added at the same temperature. Finally, the resulting product was filtered off, washed with water and dried under vacuum at 50 C.Yield: 15 g. Molar yield: 52.63%. HPLC purity 81.82%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS LESVI, S. L.; VISHNU NEWADKAR, Ravindranath; CHANGDEO GAIKWAD, Avinash; MADHUKAR HARAD, Ajay; DALMASES BARJOAN, Pere; WO2013/53739; (2013); A1;,
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Reference of 317-20-4, The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life.

General procedure: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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Synthetic Route of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(b) 4-(Phthalimido)-cyclohexanone 95 g (0.388 Mol) of 4-(phthalimido)cyclohexanol are dissolved in 600 ml of chloroform and, after the addition of 450 ml of water and 120 ml of sulfuric acid, 90 g (0.3 Mol) of potassium dichromate are added in batches. The internal temperature of the mixture is maintained at between 25 and 30 C. by slight cooling. The mixture is stirred for a further 3 hours, then the chloroform phase is separated of and the mixture extracted twice more with chloroform. After drying and concentration of the extracts 82 g (86.9% of theory) are obtained.

The synthetic route of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; US4731374; (1988); A;,
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