Author: Jessica.F

These common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, 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. Safety of 3,3-Dimethylindoline

EXAMPLE 1 STR12 In 0.7 ml of thionyl chloride, 0.13 g of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid hydrochloride (containing sodium chloride) was refluxed for 30 minutes, and volatile components were removed by distillation under reduced pressure. The residue was added to a solution of 0.15 g of 3,3-dimethylindoline and 0.15 ml of triethylamine in 2 ml of dichloromethane under ice-cooling. After stirring the mixture at room temperature overnight, 5 ml of a sodium carbonate aqueous solution was added thereto, and the mixture was extracted with chloroform. The organic layer was dried, and the solvent was removed by distillation under reduced pressure. The residue was subjected to silica gel column chromatography using chloroform/methanol as an eluent to obtain 0.11 g of 5-[(2,3-dihydro-3,3-dimethylindol-1-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole as an oily substance.

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

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5344927; (1994); A;,
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Synthetic Route of 3335-98-6, 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 3335-98-6 as follows.

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.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

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. 87-48-9, name is 5-Bromoindoline-2,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: The suspension of isatin 1a-c in hydrazine hydrate was refluxed for 5h until clear solution formation. After reaction completion the mixture was cooled down to room temperature and poured into cold water. Then pH value of the mixture was adjusted to 1-2 via concentrated hydrochloride acid addition. The reaction mixture was left at room temperature for 2-3days, the precipitate formed was filtered, washed with water and dried on air and was used without additional purification. The following compounds were obtained according to this general procedure:

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; Lozinskaya, Natalia A.; Babkov, Denis A.; Zaryanova, Ekaterina V.; Bezsonova, Elena N.; Efremov, Alexander M.; Tsymlyakov, Michael D.; Anikina, Lada V.; Zakharyascheva, Olga Yu.; Borisov, Alexander V.; Perfilova, Valentina N.; Tyurenkov, Ivan N.; Proskurnina, Marina V.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry; vol. 27; 9; (2019); p. 1804 – 1817;,
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Electric Literature of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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.

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 ML of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide.. The mixture was stirred for 1 hour, diluted with 100 ML 50% acetic acid in water and filtered.. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off-white solid.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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Electric Literature of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

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

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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These common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-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. Safety of 2-(3-Oxobutyl)isoindoline-1,3-dione

In a 10 ml reaction tube, adding phosphine nitrogen ligand L3a (0.31 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laf (43.4 mg, 0.2 mmol) with anhydrous carbonate cesium (6.50 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 af. The conversion is 100%, enantiomeric excess is 93%. 2 Af: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

The synthetic route of 2-(3-Oxobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
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Adding a certain compound to certain chemical reactions, such as: 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione, 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 1677-48-1, SDS of cas: 1677-48-1

General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.

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, 5,6-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur; Indian Journal of Heterocyclic Chemistry; vol. 23; 4; (2014); p. 411 – 418;,
Indoline – Wikipedia,
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Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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

To a solution of N-phthaloylglycine (36.3 mg, 0.177 mmol) in CH2Cl2 (1.8 mL) were added(COCl)2 (46 L, 0.532 mmol) and DMF (1 drop) at 0 C. The reaction mixture was stirred at0 C for 10 min and at room temperature for 2 h. The solvents were removed under reduced pressure. Azeotropic distillations were carried out with toluene (2 × 2 mL) under reducedpressure. The residue (acid chloride) was used for next step without further purification.To a solution of compound 5 (25.0 mg, 0.0592 mmol) and pyridine (43 L, 0.532 mmol) inCH2Cl2 (0.3 mL) was added a solution of the above crude product (acid chloride) in CH2Cl2 (0.6mL) at 0 C. The reaction mixture was stirred at 0 C for 30 min and at room temperature for 9 h.After cooling to 0 C, the reaction mixture was quenched by addition of saturated NaHCO3 aq.(5 mL). The whole mixture was extracted with CH2Cl2 (2 10 mL), and the combined organiclayers were dried with Na2SO4. After filtration and evaporation, the crude was purified by silicagel chromatography (n-hexane/EtOAc 1:1 to 1:2) to give compound 14 as a pale yellow oil (34.0mg, 94%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4702-13-0, its application will become more common.

Reference:
Article; Natori, Yoshihiro; Hwang, Candy S.; Lin, Lucy; Smith, Lauren C.; Zhou, Bin; Janda, Kim D.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1020 – 1031;,
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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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Nitroindoline

Example 13; 3-[1-(1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 13a) tert-butyl 5-nitro-2,3-dihydro-1H-indole-1-carboxylate To a stirred mixture of 5-nitroindoline (5.0 g) and Boc2O (7.07 mL) in THF (100 mL) was added DMAP (0.5 g) at room temperature. The mixture was stirred at 60 C. for 3 h. The mixture was quenched with water, treated with sat. NaHCO3aq. and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was used for the next reaction without further purification.

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; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; MIURA, Kasei; HASUI, Tomoaki; HONDA, Eiji; IMAMURA, Keisuke; KAMATA, Makoto; KAMISAKI, Haruhi; QUINN, John F.; RAKER, Joseph; CAMARA, Fatoumata; WANG, Yi; US2011/319394; (2011); A1;,
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Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-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.

General procedure: A suspension mixture of N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)thiosemicarbazide 2 (2mmol, 0.84g) and appropriate substituted isatin 3a-l (2mmol) and glacial acetic acid (0.02mL) in absolute ethanol was microwave irradiated for 5?15min (depending on substituents on benzene ring of isatins). After irradiating for 1?3min, the suspension mixture became a clear solution. The irradiation was continued in a given time. At the end of reaction process, the precipitate appeared. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature; the color precipitate was filtered with suction. The crude product was recrystallized from 96percent ethanol or mixture of toluene-96percent ethanol (2:1 in volume) to afford the title compounds of substituted isatin N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl) thiosemicarbazones 4a-l. The spectral (FT-IR, 1H NMR, 13C NMR and ESI-MS or EI-HRMS) data are in good agreement with their structures.

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Thanh, Nguyen Dinh; Giang, Nguyen Thi Kim; Quyen, Tran Ha; Huong, Doan Thi; Toan, Vu Ngoc; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 532 – 543;,
Indoline – Wikipedia,
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