Tag: M.W=100-200

Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. Safety of 7-Chloroisatin

7-Chloroisatin 1a (0.5 mmol, 90.6 mg), CuI (10 molpercent, 9.5 mg) was added to a 15-mL thick-walled pressure tube, 1,10-phenanthroline(10 molpercent, 9.0 mg) and ethyl isocyanoacetate 2 (0.6 mmol, 67.2 mg) were added, and 2 mL of toluene was added as the solvent The oil bath was 110 ¡ã C and the reaction was followed by TLC until the reaction was complete. After the end of the reaction, stop heating, transfer to a single mouth bottle spin, with PE: EA = 4: 1 column chromatography gave the product as a yellow solid which was identified as 7-chloro-3-methyleneindolone 3a by NMR and HRMS. The yield was 75percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7477-63-6, its application will become more common.

Reference:
Patent; Qingdao University of Science and Technology; Li, Ming; Yu, Le; Wen, Lirong; (14 pag.)CN106083690; (2016); A;,
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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 20870-79-5 as follows. SDS of cas: 20870-79-5

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

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:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Related Products of 52351-75-4, 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. 52351-75-4 name is 6-Methoxyindoline-2,3-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.

Intermediate- 136: 6-Methoxy-l-methylindoline-2, 3-dione:To a stirred suspension of commercially available 6-methoxyindoline-2,3-dione (0.2 g ,1.12 mmol) and sodium hydride (60% w/w dispersion in mineral oil, 0.067 g,2.79 mmol) in dry DMF ( 5 ml) was added methyl iodide (0.084 ml, 1.35 mmol) slowly at 0 C. The mixture was stirred at 0 C for 45 min and quenched with water (10 ml) at 0 C and added ethyl acetate. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2x 25 ml). The combined organic layer was washed with water (2×20 ml), followed by brine (2×20 ml), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuum to dryness to get a brown solid of 6-methoxy-l-methylindoline-2, 3-dione (0.140 g, 65%). 1H NMR (400 MHz, CDC13) delta 7.58 (d, J = 8 Hz, 1H), 6.57 (dd, J = 8 Hz, 4 Hz, 1H), 6.36 (d, J = 4 Hz, 1H), 3.93 (s, 3H), 3.22 (s, 3H); MS (ES+) m/z 191.9 (M+l), 213.9 (M+ Na)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxyindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; LUPIN LIMITED; PADIYA, Kamlesh, Jyotindra; NAIR, Prathap, S.; PAL, Ravindra, Ramsurat; CHAURE, Ganesh, Shankar; GUDADE, Ganesh, Bhausaheb; PARKALE, Santosh, Sadashiv; MANOJKUMAR, Vishwanath, Lohar; SWAPNIL, Ramesh, Bajare; SMITA, Aditya, Bhoskar; SACHIN, Dilip, Survase; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/49555; (2012); A1;,
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Reference of 16078-34-5, A common heterocyclic compound, 16078-34-5, name is 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, molecular formula is C10H11NO, 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: RuCl3nH2O (0.5 mol %), HMTA-Bz (1 mol %), amine (0.25 ml)and dry toluene (1.0 ml) were placed in a Schlenk tube. The reactionmixture was stirred under open condition to nitrogen andrefluxed for 24 h. After completion of the reaction all toluene wereevaporated under vacuo, the oxidized products were isolated fromcrude mixture with the help of column chromatography using hexane/EtOAc as eluent. The formation of products was confirmed bycomparing the 1H NMR data with literature reports.

The synthetic route of 16078-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Barteja, Parul; Devi, Preeti; Kannan, Muthukumar; Muthaiah, Senthilkumar; Journal of Catalysis; vol. 386; (2020); p. 1 – 11;,
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Adding some certain compound to certain chemical reactions, such as: 25369-33-9, name is 7-Chloroindolin-2-one, 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 25369-33-9. 25369-33-9

To a cooled (0 C.) solution of 7-chloroindolin-2-one (1.0 g, 6.0 mmol) in TFA (11 mL) was added N-bromosuccinimide (1.0 g, 6.0 mmol) portion wise, and the resulting mixture was stirred at 0 C. for 6 h. The solvent was removed in vacuo and the residue was diluted and evaporated successively with DCM (25 mL) and EtOAc (25 mL). The crude product was triturated with EtOH to provide the title compound as a white solid (861 mg, 58% yield). MS (ESI): mass calcd. for C8H5BrClNO, 244.9; m/z found, 246.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 10.92 (s, 1H), 7.52-7.48 (m, 1H), 7.38 (d, J=1.2 Hz, 1H), 3.62 (s, 2H).

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 7-Chloroindolin-2-one.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Laforteza, Brian Ngo; Lebold, Terry Patrick; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; (70 pag.)US2018/111942; (2018); A1;,
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These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, 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. 611-09-6

General procedure: The mixture of the Fe(III)(at)g-C3N4 nanocomposite (70 mg, 0.35 mmol based on Fe(III)) in aqueous media (3 ml) was dispersed for 30 min. Isatin (1 mmol) and indole (2.0 mmol) were added to the mixture and stirred in reflux conditions for an appropriate time. After the reaction was completed, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4 followed by evaporation of the solvent. The pure products were achieved by recrystallization in hot ethanol and identified by IR, 1H & 13C NMR spectral data. The nanocomposite was washed with EtOH, dried, and reused for the next run.

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 611-09-6.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6741 – 6751;,
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The chemical industry reduces the impact on the environment during synthesis 603-62-3, name is 3-Nitrophthalimide, I believe this compound will play a more active role in future production and life. 603-62-3

3-Nitrophthalimide (5 g) and hydroxylamine sulfate powder (11 g) were sequentially added to isopropanol (90 mL).Stir the reaction mixture.A solution of potassium hydroxide (6 g) in water (5 ml) was added in one portion.Get a red liquid.The temperature of the reaction solution was slowly raised to 40 C, the solution was stirred for 30 minutes, filtered,Recrystallization twice with water, dried at 80 to give 1.4g yellow needle crystal,After vacuum drying at 120 C, 1.12 g (24% yield) of yellow powder was obtained.

The chemical industry reduces the impact on the environment during synthesis 603-62-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Zaiqi Biological Co., Ltd.; Wang Zhiguo; Song Yanhong; Ma Xiujuan; Tian Beibei; Li Shijiang; Li Chao; Zhang Xin; Li Tao; (7 pag.)CN107474007; (2017); A;,
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The chemical industry reduces the impact on the environment during synthesis 19727-83-4, name is 6-Nitroindoline, I believe this compound will play a more active role in future production and life. 19727-83-4

Step A 1-Methyl-6-nitroindoline Potassium bis(trimethylsilyl)amide (67 ml of a 0.5M toluene solution) was added slowly to a stirred solution of 6-nitroindoline (5.0 g) in anhydrous tetrahydrofuran (200 ml) at -78 C. under a nitrogen atmosphere. Iodomethane (2.09 ml) was added then the reaction mixture was allowed to warm to room temperature then stirred overnight. Methanol (5 ml) was added then the solution was evaporated to dryness. The residue was dissolved in diethyl ether (300 ml), washed with water, saturated brine then dried (magnesium sulphate) and evaporated to dryness. The crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)?30% ethyl acetate/petroleum ether (60-80) and the product crystallized from diethyl ether/petroleum ether (60-80) to afford 0.9 g.

The chemical industry reduces the impact on the environment during synthesis 19727-83-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck, Sharp & Dohme, Ltd.; US5696110; (1997); A;,
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59-48-3, Adding some certain compound to certain chemical reactions, such as: 59-48-3, name is Indolin-2-one, 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 59-48-3.

An oven-dried flask was charged with oxindole (133 mg, 1 mmol, 1 equiv) before the addition of anhydrous DMF (0.8 M, 1.25 mL) and dibromoethane (94 muL, 1.1 mmol, 1.1 equiv). The solution was then cooled to 0 C before the addition of NaH (60% dispersion in mineral oil, 180 mg, 4.5 mmol, 4.5 equiv) portionwise over 20 min. The mixture was then warmed to r.t. and stirred overnight, then the reaction was quenched with H2O (3 mL) and the mixture was extracted with EtOAc (5 mL). The organic layers were then washed with H2O (2 ¡Á 5mL) and brine (2 ¡Á 5 mL) and passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc/petroleum ether, 20-40%) to afford the desired product. Yield: 23 mg (14%); red/brown amorphous solid. IR (solid): 3200, 1701, 1684, 1671, 1627, 1474, 1357 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.34 (s, 1 H), 7.19 (t, J = 7.7 Hz, 1 H), 7.01 (t, J = 7.5 Hz, 1 H), 6.96 (d, J = 7.7 Hz, 1 H), 6.83 (d, J = 7.4 Hz, 1 H), 1.76 (d, J = 3.0 Hz, 2 H), 1.54 (d, J = 2.9 Hz, 2 H). 13C NMR (101 MHz, CDCl3): delta = 179.1, 140.6, 131.3, 126.7, 122.0, 118.6, 109.7, 27.4, 19.5. HRMS (NSI): m/z [M + H]+ calcd for C10H10NO: 160.0757; found: 160.0753.

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 59-48-3.

Reference:
Article; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
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Adding a certain compound to certain chemical reactions, such as: 3484-35-3, name is 5-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 3484-35-3, 3484-35-3

General procedure: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
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