Month: June 2021

Electric Literature of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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 mixture of 5-nitroindolin-2-one (15 g, 84 mol)in 1,2-dichioroethane (300 mL) was added POBr3 (23 g,80 mmol) . The mixture was heated to 90C and stirred for0.5 h. Then the reaction was cooled just below 90C andimidazole (6.9 g, 101 mmcl) was added in one portion. The mixture was stirred at 90C for 2 h. The reaction was quenched by ice water (200 mL) and then extracted with DCM (200 mL x 3) . The combined organic phase was washed with brine (300 mL x 2), dried over anhydrousNa2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=10:1 to 5:1 to 3:1) to give the title compound (11 g, 46 mmol, 54%yield) as a solid.H NMR (400 MHz, DMSO-d6) oe (ppm) 6.86 (s, 1H), 7.49 (d,J=9.2 Hz, 1H) , 7.91 – 8.07 (m, 1H) , 8.50 (s, 1H) , 12.63(br 5, 1H)

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

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; NAKAMURA, Tsuyoshi; AKIU, Mayuko; TSUJI, Takashi; TANAKA, Jun; TERAYAMA, Koji; YOKOYAMA, Mika; PINKERTON, Anthony, B.; SESSIONS, Edward, Hampton; (289 pag.)WO2020/10252; (2020); A1;,
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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 446292-08-6 as follows. category: indolines-derivatives

10 g (0.024 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), 7.12 mL of methylamine (40% aqueous solution, 0.083 mol) and 150 mL of methanol were charged in a 1 L autoclave and heated to reflux temperature (65.0C) for 1 hour. Afterwards, the reaction mass was cooled to 25-30C and transferred to another flask. Then, 9.9 g (0.095 mol) of malonic acid in 50 mL of methanol were added dropwise within 30 min. Then, the reaction mass was stirred to 25-30 C for 24 hours. The solid obtained after filtration was stirred in 100 mL of ethanol at 25 C for 1 hour. Finally, the solid obtained was filtered off and dried under vacuum at 50 C.Yield: 5.9 g. Molar yield: 62.89%. HPLC purity: 99.15%. MP.: 189.14 C (DSC).XRD (2Th): 18.0, 20.1 , 21 .6, 23.0, 24.0, 24.1 , 24.3, and 27.6 as shown in figure 5. IR (cm”1): 3473.0, 2912.5, 2691.9, 1745.6, 1661 .6, 1598.7, 1519.5, 1459.3, 1475.5, 1434.8, 1409.9, 1378.0, 1343.0, 1328.9, 131 1.1 , 1288.9, 1263.3, 1227.1 , 1 162.2, 1 136.7, 1 125.3, 1060.4, 1037.9, 1002.6, 982.6, 919.5, 858.4, 833.0, 777.3, 752.5, 710.8, 689.0, 671.8, 597.5, 556.5, 547.3, 526.1 , 516.0, 505.8, 495.9, 486.1 , 475.3, 465.5 and 455.6 as shown in figure 6. Example

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

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 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

A. Preparation of (2a) where R3 is 4-chloro To a solution of 4-chlorophthalimide (60 g) in 1 liter of tetrahydrofuran was added borane-methyl sulfide complex (100 ml of 10M), and the mixture was refluxed overnight. After cooling, 100 ml of 6N hydrochloric acid was added slowly, the mixture refluxed for 2 hours, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting aqueous solution washed with ethyl acetate. The aqueous layer was then basified with ammonium hydroxide and extracted with methylene chloride. Solvent was removed from the extract, and the residue distilled under vacuum to give 4-chloroisoindoline, a white solid, m.p. 48-50 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloroisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5726197; (1998); A;,
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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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5,7-Dimethylindoline-2,3-dione

General procedure: To asolution of isatin 3 (1.0mmol), 2-aminopyridine 2 (1.35mmol)andisocyanide 4 (1.35mmol) in 4mL of n-butyl alcohol was added HClO4 (1.0mmol), and the reaction mixture was stirred under refluxfor 8 h. After cooling to room temperature, the precipitate was collected by filtration, rinsed with ethanol and dried to afford the target compound 1.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Bo; Tao, Chuanye; Shao, Taofeng; Gong, Jianxian; Che, Chao; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1487 – 1492;,
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Synthetic Route of 102359-00-2, The chemical industry reduces the impact on the environment during synthesis 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, I believe this compound will play a more active role in future production and life.

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)-1 /-/-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-c/6) delta ppm: 13.52 (s,1 H), 12.5 (bs,1 H), 1 1 .19 (s,1 H), 8.37 (s,1 H), 7.78 (s,1 H), 7.77 (d,1 H), 6.96 (d,1 H), 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+HV392.

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, 2-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; ULLRICH, Axel; FALCENBERG, Mathias; OeRFI, Zoltan; KERI, Gyoergy; OeRFI, Laszlo; HORVATH, Zoltan; SZOKOL, Balint; DOBOS, Judit; NEMES, Zoltan; WO2015/22437; (2015); A1;,
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7477-63-6, name is 7-Chloroisatin, 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. COA of Formula: C8H4ClNO2

General procedure: To a mixture of isatin or isatin derivatives (1 mmol) in DMF (1.5 mL) was added dried K2CO3 (165.5 mg, 1.2 mmol). The resulting mixture was stirred at 70oC for 1 hour, then 83 mg of KI (0.5 mmol) was added followed by slow addition of a solution of 3,4,5-trimethoxybenzyl clorid (216.7 mg, 1 mmol) in DMF (1 mL). The reaction mixture was stirred for a further 3 hours at 80oC, then cooled to room temperature. Cold water (20 mL) was slowly added to the cooled reaction mixture and pH was adjusted to ~ 6 by a solution of HCl 5percent to generate yellowish to brown precipitates, which were filtered, washed by cold water until neutrality. The precipitates were recrystallized by EtOH/H2O and dried at 60oC under vacuum.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huan, Le Cong; Pham-The, Hai; Le-Thi-Thu, Huong; Thao, Tran Phuong; Que, Do Nguyet; Trang, Nguyen-Thu; Dung, Phan Thi Phuong; Pyo, Minji; Han, Sang-Bae; Thuan, Nguyen Thi; Nam, Nguyen-Hai; Letters in drug design and discovery; vol. 15; 4; (2018); p. 375 – 387;,
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Reference of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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 compound 9 (12.0 g, 40.5 mmol) and potassium carbonate (14.0 g, 101 mmol) in THF (150 mL) was added dropwise an excess of a dimethylamine aqueous solution (26% wt) (39 mL, 202.5 mmol) and the reaction mixture was refluxed for 24 h. After cooling, the solution was filtered and the precipitate was washed with THF (200 mL). After concentration under reduced pressure, the filtrate afforded a biphasic residue that was decanted. The oily layer was separated to yield a first fraction of compound 13a. The remaining aqueous layer was extracted with EtOAc (2 × 75 mL), the organic extracts were combined, dried over MgSO4, filtered and evaporated under vacuum to afford a supplementary fraction of compound 13a. The two fractions (6.95 g, 34.0 mmol) were combined and engaged directly in the next step without further purification. Yield 84%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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Synthetic Route of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: GN/SO3H (80 mg) was added to the 3 mL of EtOH/water (1:1) and dispersed for 30 min. Then, malononitrile (1 mmol), isatin (1 mmol), and dimedone (1 mmol) were added to the mixture and the mixture was heated to reflux and kept at this temperature for an appropriate time. After the time of reaction was completed, water was separated by centrifuging followed by extracting the crude product by ethyl acetate. The solvent was dried using Na2SO4 and removed from the reaction by evaporation with a rotary evaporator. Finally, the crude product was recrystallized in hot ethanol to achieve the pure product. The GN/SO3H nanocomposite was washed and reused several times.

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

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6979 – 6993;,
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Related Products of 40314-06-5, A common heterocyclic compound, 40314-06-5, name is 5-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.

he starting materials were 5-methyl-phthalimide (300 mg, 1.86 mmol) and K2CO3 (257.39 mg, 1.86 mmol), in 2 mL of DMF. 6-bromoethyl hexanoate (0.33 mL, 1.86 mmol) was added to this solution, and the reaction mixture was heated at 120ºC for 24 hours. After the reaction time elapsed, it is diluted with water and an extraction with ethyl acetate (3x5mL) was performed, the organic phase was dried on MgSO4, filtered and concentrated in the rotary evaporator. A yellow liquid was obtained (564 mg, quantitative yield). 1H-NMR (C3D6O): delta 7.70 (d, 1 H, Harom, J = 7.8 Hz); 7.61 (d, 2H, Harom, J = 8.4 Hz); 4.03 (c, 2H, O-CH2CH3, J = 7.1 Hz); 3.61 (t, 2H, N-CH2, J = 7.1 Hz); 2.50 (s, 3H, Ar-CH3); 2.26 (t, 2H, CH2-CO, J = 7.4 Hz); 1.70 – 1.57 (m, 4H, CH2); 1.40 – 1.32 (m, 2H, CH2); 1.16 (t, 3H, O-CH2CH3, J = 7.2 Hz). 13C-NMR (C3D6O): 172.7 (COOEt); 168.1 (CO); 168.0 (CO); 145.4 (Carom); 134.5 (CHarom); 132.8 (Carom); 129.8 (Carom); 123.4 (CHarom); 122.8 (CHarom); 59.6 (O-CH2CH3); 37.4 (N-CH2); 33.6 (CH2-CO); 28.1 (CH2); 26.1 (CH2); 24.4 (CH2); 21.0 (Ar-CH3); 13.7 (O-CH2CH3). HR LSIMS: Calculated for C17H21NO4Na (M+Na)+ 326.1368; found 326.1371 (deviation -0.9 ppm).

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; Universidad De Granada; EP2045239; (2009); A1;,
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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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., name: 5-Nitroindolin-2-one

To a suspension of the lactam (10.0 g, 56 mmol) in 200 ml of 1 ,2-dichloroethane, was added POBr3 (15.3g, 53.2 mmol) at RT. The resulting mixture was heated at reflux temperature in a 9OC oil bath for 0.5 hour (the reaction formed a copious amount of precipitate, and an oil bath was preferred over a heating mantle, as it provided gentle heating and avoided a darkening of the precipitate). The reaction was cooled just below reflux temperature, and imidazole (4.57 g, 62 mmol) was added in one portion. The resulting gummy suspension was heated at reflux temperature in an oil bath for another 2 hours. The reaction was cooled to RT, and 100 mL of ice-water was added. Solid NaHCO3 (ca. 50 g) was added to the mixture until no further gas was evolved. The suspension was extracted with DCM (4chi), and the combined DCM extracts were washed with 300 mL of brine. The DCM extracts were filtered through silica gel and concentrated to dryness to afford a crude product. The crude product was recrystallized from chloroform to give 5.41 g of the desired compound as a white solid. The filtrate was concentrated to dryness, and the residue was purified by flash column chromatography (30% EtO Ac/Hex) to give an additional 2.6 g of desired product. MS (ESI) m/e (MH-H+): 242.

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); A1;,
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