Tag: M.W=100-200

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 13220-46-7 as follows. name: 4-Methylindolin-2-one

Example 76 (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 4-methyl-1,3-dihydro-indol-2-one (12 mg, 0.08 mmol) were dissolved in 156 mul of ethanol, and added with 4.4 mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45 C. for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml*2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 76 (12 mg, yield 30%) as a orange solid.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

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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Reference of 19727-83-4, 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. 19727-83-4 name is 6-Nitroindoline, 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.

General procedure: Into a Schlenk tube (volume: ca. 20 mL) connected to a balloon partially filled with Ar gas, Pd/LDH (75 mg, Pd: 3 mol %), 4-isopropylpiperidine (0.5 mmol), decane (internal standard, 0.1 mmol), octane (2.0 mL), and a Teflon-coated magnetic stir bar were successively placed, and the reaction mixture was vigorously stirred at 120 C, in 1 atm of Ar. After the reaction was completed, the conversion of 4-isopropylpiperidine and the yield of 4-isopropylpyridine were determined by GC analysis. The reactions of piperidine and 4-methylpiperidine were conducted in a test tube with an Ar balloon. During these reactions, the upper side of the test tube was cooled by refrigerant (-5 C).

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

Reference:
Article; Oyama, Takashi; Yatabe, Takafumi; Jin, Xiongjie; Mizuno, Noritaka; Yamaguchi, Kazuya; Chemistry Letters; vol. 48; 6; (2019); p. 517 – 520;,
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Synthetic Route of 7477-63-6, The chemical industry reduces the impact on the environment during synthesis 7477-63-6, name is 7-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50¡ãC for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 ¡Á 30 mL) and cold aqueous ethanol (2 ¡Á 1 mL) to afford pure product 4.

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

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
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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., SDS of cas: 20870-79-5

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

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

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Electric Literature of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-chloro-2-subsituted quinazoline (1.0 mmol), 5-methoxyindoline or 6-substituted-1,2,3,4-tetrahydroquinoline or 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[b or c]azepine (1.2 mmol) and sodium bicarbonate (3.0 mmol) were added to anhydrous ethanol (5 ml), reacted at room temperature or under refluxing condition for 1-10 h. After the end of reaction, the reactants were poured into ice-water, adjusted pH with 2N hydrochloric acid to 3, extracted with ethyl acetate, dried with anhydrous sodium sulfate. The solvent was removed under vacuum, and the resultant crude product was separated by silica gel column chromatography (eluent: ethyl acetate and petroleum ether for gradient elution, ethyl acetate 5%-80%).; Compound 8 was obtained after reaction at room temperature for 1 h, which was yellow solid, 242 mg, yield 77%, melting point 116-117C. 1H NMR (CDCl3): 6 ppm 2.70 (3H, s, CH3), 3.19 (2H, t, J = 8.0 Hz, 3′-CH2), 3.81 (3H, s, OCH3), 4.45 (2H, t, J = 8.0 Hz, 2′-CH2), 6.69 (1 H, dd, J = 8.8 Hz and 2.4 Hz, ArH-6′), 6.86 (1 H, d, J = 2.4 Hz, ArH-4′), 7.37 (2H, m, ArH-7′ and ArH-6), 7.73 (1 H, t, J = 7.6 Hz, ArH-7), 7.84 (1 H, d, J = 8.4 Hz, ArH-5), 8.03 (1 H, d, J = 8.4 Hz, ArH-8). MS m/z (%) 292 (M+H+, 100).

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

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Militaty Medical Sciences P.L.A.; XIE, Lan; WANG, Xiaofeng; LEE, Kuo-Hsiung; EP2857393; (2015); A1;,
Indoline – Wikipedia,
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Application 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.

30 g (165.2 mmol) of 5-chloroisoindolin-1,3-dione, sodium tertbutoxide 198.2 mmol, methyl iodide 198.2 mmolAnd 200 mL of toluene were mixed, refluxed, heated for 30 minutes, and 1.6 mmol of tetrakistriphenylphosphinepalladium was added thereto, followed by stirring for 3 hours in a reflux state. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was recrystallized twice from chloroform and hexane to give 23.9 g of Compound 1-G (yield 74%).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; SUNGKYUNKWAN University Research & Business Foundation; Yoon Hong-sik; Hong Wan-pyo; Kang Yu-jin; Kim Jin-ju; Han Si-hyeon; (93 pag.)KR2019/101894; (2019); A;,
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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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., SDS of cas: 3485-84-5

EXAMPLE III-9 tert-Butyl 2-{3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]phenoxy}-2-methyl-propanoate In an autoclave, 14.93 g (47.37 mmol) of the compound from Example III-6, 10.25 g (59.21 mmol) of vinylphthalimide, 0.39 g (1.27 mmol) of tris-o-tolylphosphine, 0.07 g (0.32 mmol) [lacuna] and 21.78 g (215.23 mmol) of triethylamine are heated at 130 C. Water/methanol is added, and the precipitate is then filtered off with suction and recrystallized from cyclohexane/ethyl acetate. Yield: 66%. 1H-NMR (200 MHz, CDCl3): delta=1.40 (s, 9H), 1.50 (s, 6H), 6.73 (dd, 1H), 6.86-6.93 (m, 1H), 7.16 (t, 1H), 7.21-7.34 (m, 2H), 7.43 (d, 1H), 7.80-8.00 (m, 4H). MS (DCI/NH3): 425 [M+NH4+].

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; Urbahns, Klaus; Woltering, Michael; Nikolic, Susanne; Pernerstorfer, Josef; Hinzen, Berthold; Dittrich-Wengenroth, Elke; Bischoff, Hilmar; Hirth-Dietrich, Claudia; Lustig, Klemens; US2003/32671; (2003); A1;,
Indoline – Wikipedia,
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Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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. Recommanded Product: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Merck, Sharp & Dohme, Ltd.; US5696110; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Recommanded Product: Isoindoline

To a stirred suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (0.53 g, 2.04 mmol, 1 eq.) and potassium carbonate (0.56 g, 4 mmol, 2 eq.) in N,N-dimethylformamide (5 mL) was added isoindoline (280 mu^, 2.45 mmol, 1.2 eq.). The resulting mixture was then stirred at room temperature for 17 hours. The solvent was removed in vacuo and the crude product was partitioned between water and dichloromethane, the layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography using a 10 – 100 % ethyl acetate in wo-hexane gradient to afford methyl 4- (isoindolin-2-ylmethyl)-3-methoxybenzoate as a red liquid (0.417 g, 70 % yield). NMR (400 MHz, CDC13) 7.66 (1H, d, J=7.8 Hz), 7.55-7.53 (2H, m), 7.18 (4H, s), 4.0-3.98 (6H, m), 3.92-3.91 (6H, m).

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Indoline – Wikipedia,
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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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A mixture of 3,3-dimethylindoline (2.1 g, 14.26 mmol) and 2-bromoethanamine hydrobromide (3.215 g,15.69 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purified bypreparative HPLC to give the title compound (1.9 g). LCMS m/z = 191.4 [M+H]+; 1H NMR (400 MHz,CD3OD) delta ppm 1.31 (s, 6H), 3.14 (s, 2H), 3.19 (t, 2H, J = 6.1Hz), 3.33 (t, 2H, J = 6.1 Hz), 6.60 (d, 1H, J = 7.9Hz), 6.70-6.76 (m, 1H), 7.01-7.09 (m, 2H).

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; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem