Category: 61-70-1

Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, 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 61-70-1, Formula: C9H9NO

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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, 1-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 61-70-1

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO

General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60-70C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95%) togive N-alkylated isatins as red crystalls in 37-92% yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2-4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4¡¤H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47-96% yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60% dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of -15 C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3′-indolin]-2′-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3′-indolin]-2′-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7-11).

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; Buev, Evgeny M.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 37; (2018); p. 3409 – 3412;,
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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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Product Details of 61-70-1

To a dried round-bottomed flask equipped with a magnetic stir bar was added 1-methylindolin-2-one (0.74 g, 5 mmol), Lawesson?s Reagent (1.07 g, 2.65 mmol) in dry CH2Cl2 (3.60 mL). The reaction was held at the room temperature for 20 h, followed by concentration in vacuo. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography to get 1-methylindoline-2-thione 1 (0.69g, 85% bright yellow solid).

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; Zhou, Shiping; Xiao, Genhua; Liang, Yun; Tetrahedron Letters; vol. 58; 4; (2017); p. 338 – 341;,
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Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, 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 61-70-1, SDS of cas: 61-70-1

No. A1-173: 1-(3-Bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (0127) (0128) Together, 1-methyl-1,3-dihydro-2H-indol-2-one (2.00 g, 14 mmol) and 1,2-dibromoethane (3.83 g, 20 mmol) were dissolved in abs. N,N-dimethylformamide (15 ml), sodium hydride (1.68 g, 42 mmol, 60% strength dispersion) was then added carefully a little at a time at a temperature of 10-15 C. and the mixture was stirred for another one and a half hours. Methanol and aqueous ammonium chloride solution were then added to the reaction mixture, and the aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2500 mg, 92% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.25 (m, 1H), 7.03 (m, 1H), 6.91 (d, 1H), 6.83 (d, 1H), 3.30 (s, 3H), 1.73 (m, 2H), 1.52 (m, 2H). 1?-Methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2.50 g, 13 mmol) was added to glacial acetic acid (23 ml), and fuming nitric acid (4 ml) was then added slowly and carefully. The resulting reaction mixture was stirred at room temperature for 30 minutes and then slowly diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium carbonate solution and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1800 mg, 57% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.25 (dd, 1H), 7.74 (d, 1H), 6.97 (d, 1H), 3.36 (s, 3H), 1.88 (m, 2H), 1.69 (m, 2H). In the next step, 1?-methyl-5-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1.80 g, 8 mmol) and tin(II) chloride dihydrate (7.45 g, 33 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1226 mg, 79% of theory) as a colorless solid. 1H-NMR (400 MHz, CDC138, ppm) 6.71 (d, 1H), 6.60 (dd, 1H), 6.25 (d, 1H), 3.52 (br. s, 2H, NH), 3.24 (t, 2H), 1.71 (m, 2H), 1.43 (m, 2H). In a round-bottom flask under argon, 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (130 mg, 1.0 equiv.) and (3-bromophenyl)methanesulfonyl chloride (261 mg, 1.4 equiv.) were dissolved together in abs. acetonitrile, pyridine (0.11 ml, 2.0 equiv.) and dimethyl sulfoxide (0.03 ml, 0.60 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1-(3-bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (235 mg, 81% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (m, 1H), 7.39 (m, 1H), 7.29 (m, 1H), 7.24 (m, 1H), 7.04 (m, 1H), 6.87 (d, 1H), 6.65 (d, 1H), 6.26 (s, 1H, NH), 4.13 (s, 2H), 3.30 (s, 3H), 1.78 (m, 2H), 1.54 (m, 2H). 13C-NMR (150 MHz, CDCl3 delta, ppm) 176.8, 141.7, 133.7, 132.6, 132.1, 130.8, 130.4, 129.5, 122.6, 120.8, 113.3, 108.3, 56.8, 27.4, 26.7, 19.7.

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; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); 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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C9H9NO

HNO3 (70% aqueous, 1.41 g, 22.4 mmol, 1.7 equiv) was slowly added to a solution of 1-methylindolin-2-one (2.00 g, 13.6 mmol, 1 equiv) in concentrated H2SO4 (8 mL) at 0C with stirring. After being stirred for 30 min, the mixture was poured onto a water/ice mixture (200mL). The resulting precipitate was collected by filtration and washed with water (250 mL) to give pure 1-methyl-5-nitroindolin-2-one (2.3g, 88%) as a tan solid.

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; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
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Synthetic Route of 61-70-1, 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 61-70-1 as follows.

To a round-bottom flask containing a solution of N-methyl-2-oxindole (4.85 g, 33 mmol) in acetic anhydride (36 mL, 381 mmol), DMAP (118 mg, 0.96 mmol) was added. The mixture was heated at 140 C for 5 h. The mixture was evaporated under reduced pressure, the crude residue was dissolved in MeOH (80 mL) and a solution of KOH (18 g, 321 mmol) in MeOH (120 mL) at 0 C was added. The solution was stirred at r.t. for 22 h then cooled in an ice-bath at 0 C and 12 M aqueous HCl was added until pH 3. At this point, H2O (140 mL) was added and the solution was extracted with EtOAc (3 140 mL). The organic phases were dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (hexane/EtOAc) to give pure 2a. Yield: 5.5 g (88%); purple solid; mp 109-110 C (hexane/EtOAc) (Lit. 12 110-111 C).

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ortega-Martinez, Aitor; Molina, Cynthia; Moreno-Cabrerizo, Cristina; Sansano, Jose M.; Najera, Carmen; Synthesis; vol. 49; 23; (2017); p. 5203 – 5210;,
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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 61-70-1 as follows. SDS of cas: 61-70-1

Add sodium hydride (60%, 1.4 g, 35.4 mmol) portionwise to the solution of 1-methylindolin-2-one (2.6 g, 17.7 mmol) in DMF (10 mL) at 0 C., stir for 30 min. Then add 1,2-dibromoethane (3.31 g, 17.7 mmol) to the mixture, stir the resulting mixture at room temperature overnight. Pour the reaction mixture to ice water, extract with ethyl acetate (100 mL*2), and wash the combined organic layers with brine (50 mL), dry over anhydrous sodium sulfate. Concentrate under reduced pressure, purify the residue by chromatography (silica gel, EtOAc_PE=1:3) to provide the title compound (1.5 g, 50.0%). MS: (M+1): 174.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); 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 61-70-1 as follows. COA of Formula: C9H9NO

N-methyl-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 bottles, The reaction mixture was then stirred at 25 C, the reaction was monitored by TLC or GC, and the reaction was complete with the reaction of N-methyl-2-indolone, The organic phase was extracted with ethyl acetate and the organic phase was combined. The organic phase was dried over anhydrous sodium sulfate, and the organic phase was dried over anhydrous sodium sulfate. The organic phase was dried over anhydrous sodium sulfate, The residue was isolated by column chromatography (n-hexane / ethyl acetate) to give the desired product N-methyl-isato-3-oxime I-2 in 75% yield.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

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. 61-70-1, name is 1-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylindolin-2-one

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

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 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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