Category: 20870-79-5

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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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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20870-79-5, name is 5-Nitroindolin-2-one, 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. Safety of 5-Nitroindolin-2-one

General procedure: To a suspension of 5-nitro-3-substituted-2-oxindole derivatives 8-12 or commercially available 5-nitroindolin-2-one (1 mmol) in amixture of ethanol and water (10 mL, 4:1 v/v) was added iron powder (560 mg.10 mmol,10 equiv.) and NH4Cl (134 mg, 2.5 mmol,2.5 equiv.). The mixture was refluxed for 2 h, cooled and filteredthrough Celite. The filtrate was diluted with water (5 mL) andextracted with dichloromethane (3 x 10 mL). The combinedorganic layers were washed with water (10 mL) and brine (10 mL),dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by crystallization withethyl ether.

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

Reference:
Article; Romagnoli, Romeo; Baraldi, Pier Giovanni; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Salvador, Maria Kimatrai; Lopez-Cara, Luisa Carlota; Bortolozzi, Roberta; Mattiuzzo, Elena; Basso, Giuseppe; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 258 – 270;,
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Application of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Di-tert-butyl dicarbonate (54.6 g, 0.25 mol) and sodium hydrogen carbonate (75.6 g, 0.90 mol) were added to a solution of 5-nitroindolin-2-one (17.8 g, 0.10 mol) in 1500 mE THF at room temperature in a nitrogen atmosphere and were stirred for 67 h. The mixture was then stirred for a further 50 h at 50 C., and the reaction solution was then filtered. The filtrate was evaporated until dry, and water was rubbed into the residue, which was then sucked away again and rinsed again with watet Afier the drying in a vacuum, tert-butyl 5-nitro-2-oxo-indolin-1 -carboxylate in the form of a light-brown powder was obtained (20.8 g, 75%). ?RNMR (300 MHz, d6-DMSO): oe=1.61 (s, 9R,tHu), 3.87 (s, 2R, H2), 7.89 (d, 1R, H7), 8.20 (s, 1R, H4),8.25 (d, 1R, H6). ?3C NMR (100 MHz, DMSO): 28.0 (CR3), 36.3(C2), 84.8 (C(CH3)), 114.9 (C7), 120.1 (C4), 124.4 (C6),126.5 (C9), 143.8 (C5), 146.6 (C8), 148.8 (C=O), 177.0(C2).

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

Reference:
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Nitroindolin-2-one

The commercial 5-nitroindolin-2-one (1.00 g, 5.61 mmol) was hydrogenated in EtOH (70 mL) in the presence of 10% Pd-C (315 mg, 2.97 mmol) for 4 h. Then the catalyst was filtered off through Celite, the Celite rinsed with additional EtOH and the solution was evaporated, to give 17 as a brown solid (698 mg, 4.71 mmol, 84% yield). 1H NMR (CD3OD): delta 3.43 (s, 2H, CH2); 6.63-6.65 (m, 2H, Ar); 6.73-6.74 (m, 1H, Ar) ppm. Anal. (C8H8N2O) Calc%: C 64.85, H 5.44, N 18.91; Found%: C 65.03, H 5.49, N 18.83.

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 20870-79-5.

Reference:
Article; Sestito, Simona; Nesi, Giulia; Daniele, Simona; Martelli, Alma; Digiacomo, Maria; Borghini, Alice; Pietra, Daniele; Calderone, Vincenzo; Lapucci, Annalina; Falasca, Marco; Parrella, Paola; Notarangelo, Angelantonio; Breschi, Maria C.; Macchia, Marco; Martini, Claudia; Rapposelli, Simona; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 274 – 288;,
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Related Products of 20870-79-5, 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 20870-79-5 as follows.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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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. Safety of 5-Nitroindolin-2-one

Di-tert-butyl dicarbonate (5.51 g, 25.27 mmol) and sodium hydrogen carbonate (12.73 g, 151.65 mmol) were added to a stined solution of 5-nitroindolin-2-one (3.0 g, 16.85 mmol) in tetrahydrofuran (150 mL) and the mixture was heated to 60 C. After 3h the reaction mixture was cooled and filtered, the filtrate was concentrated in reduced pressure to obtain a crudecompound. The obtained crude was purified by silica gel chromatography using a mixture of10% ethyl acetate/hexane as an eluent to get the desired compound as a white solid (3.68 g,5 1%). ?H-NMR (300 MHz, DMSO- d6) oe 8.3 (m, 1H), 8.2 (s, 1H), 7.9 (m, 1H), 3.8 (s, 2H), 1.5(s, 9H); LC-MS: m/ LC-MS: 278.8 (M+H).

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

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UJJINAMATADA, Ravi Kotrabasaiah; SAMAJDAR, Susanta; HOSAHALLI, Subramanya; ABBINENI, Chandrasekhar; (70 pag.)WO2018/109650; (2018); A1;,
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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.

Preparation of 5-amino-oxindole (2) To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

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

Reference:
Patent; Pfizer Inc; US2005/256145; (2005); A1;,
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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Example 159b 5-amino 1,3-dihydro-indol-2-one A mixture of 1.5 g (8.4 mmol) of 5-nitro-1,3-dihydro-indol-2-one, 150 mg of Pd/C 10%, and 50 ml MeOH in 100 ml of EtOAc was placed on Parr hydrogenator and charged with 45 psi of Hydrogen gas. The mixture was shaken for 2 hrs. The mixture was filtered and the solvent was removed in vacuo to yield 5-amino 1,3-dihydro-indol-2-one (1.22 g, 98%): 1H NMR (DMSO-d6): delta3.27 (s, 2H), 4.6 (s, 2H), 6.34 (dd, J1=2 Hz, J2=8.1 Hz, 1H), 6.45 (m, 2H), 9.88 (s, 1 H). APCI-MS: m/z 147 (m-H)-.

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

Reference:
Patent; Glaxo Wellcome Inc.; US6268391; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. category: indolines-derivatives

Step 2 5-Amino-1,3-dihydro-indol-2-one 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
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