Category: indolines-derivatives

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 25369-33-9 as follows. name: 7-Chloroindolin-2-one

To a suspension of AlCl3 (13.4 g, 0.10 mol) in methylene chloride (40 mL) is added a solution of 7-Chlorooxindole (0.10 mol) and chloroacetyl chloride (8 mL, 0.10 mol) at 0 C. The solution is warmed to ambient temperature for two hours and poured onto ice and extracted with methylene chloride, washing with saturated bicarbonate solution, brine, and drying over MgSO4 would provide the desired chloroketone.

According to the analysis of related databases, 25369-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, 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. SDS of cas: 21857-45-4

To a solution of 5-methoxyindoline (175 mg, 1.17 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (55%, 70 mg, 1.6 mmol) at 0 C. After the reaction mixture was stirred at the same temperature for 30 min, (2-bromoethyl)benzene (0.22 mL, 1.6 mmol) was added with additional stirring at room temperature overnight. After the reaction mixture was quenched with water at 0 C., the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 85/15) to obtain 5-methoxy-1-phenethylindole (95 mg, 32%).

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

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 912999-79-2, name is 5-Chloroisoindoline hydrochloride, molecular formula is C8H9Cl2N, 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: 912999-79-2

A mixture of Compound 151A (340 mg, 2.36 mmol) and 1-(azidomethyl)-4- methoxybenzene (500 mg, 3.07 mmol) in toluene (15 mL) was stirred at 110 C for 48 hours. The reaction mixture was concentrated and purified by column chromatography on silica gel using ethyl acetate- hexane as eluent to afford a Mixture 151B. LC-MS (ESI) m/z: 278 [M+H]._A Mixture 151B (60 mg, 0.217 mmol) and thionyl chloride (0.45 mL) in methylene chloride (10 mL) was stirred at 50 C for 5 hours. The reaction mixture was concentrated to give isic, which was used directly in the next step without further purification.LC-MS (ESI) m/z: 296 [M+H]._ A Mixture 151C (74 mg, 0.2 17 mmol), 5-chloroisoindoline (38 mg, 0.248 mmol), and K2C03 (60 mg, 0.43 5 mmol) in DMF (6 mL) was stirred at 60 C for 5 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC to afford a Mixture 151D. LCMS (ESI) m/z: 413 [M+H]t

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 912999-79-2, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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 4-Bromoisatin

General procedure: To mixture of isatins (1 mmol), malononitrile (1 mmol), and dimedone or 4-hydroxycoumarin or barbituric acids (1 mmol) in ethanol (4 mL), 5mg of Fe3O4APTPOSS MNPs added as the catalyst, and the mixture was stirred for an appropriate time at room temperature (Table 2). The reaction was monitored by TLC. After completion of the reaction, precipitate was filtered and dried in a drying oven to furnish 2-aminopyrano-3-carbonitriles.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20780-72-7, its application will become more common.

Reference:
Article; Safaei-Ghomi, Javad; Nazemzadeh, Seyed Hadi; Shahbazi-Alavi, Hossein; Catalysis Communications; vol. 86; (2016); p. 14 – 18;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 19727-83-4

EXAMPLE 128 Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h. The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Guoqing; Adams, Jeffrey; Bemis, Jean; Booker, Shon; Cai, Guolin; Pietro, Lucian Di; Dominguez, Celia; Elbaum, Daniel; Germain, Julie; Geuns-Meyer, Stephanie; Handley, Michael; Huang, Qi; Kim, Joseph L.; Kim, Tae-Seong; Kiselyov, Alexander; Ouyang, Xiaohu; Patel, Vinod F.; Smith, Leon M.; Stec, Markian; Tasker, Andrew; Xi, Ning; Xu, Shimin; Yuan, Chester Chenguang; Croghan, Michael; US2003/125339; (2003); A1;,
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, Computed Properties of C8H9N

Will Isoindoline (58 muL, 0.5 mmol),And a stirrer is placed in the reaction tube,After replacing the inert gas,DMF (193 muL, 2.5 mmol) was added, and the reaction tube was sealed.The reaction tube was placed in a 150 C oil bath reactor and the reaction was stirred for 96 hours.After cooling to room temperature, it was diluted with 15 mL of water and extracted with ethyl acetate three times, 15 mL each time.The combined extracts were dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate: petroleum ether = 1:3 (1% triethylamine) as eluent. Get pure.Black oily liquid with a yield of 80%.

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

Reference:
Patent; Xiangtan University; Gong Xing; Yin Jiawen; Cai Changqun; (15 pag.)CN109293569; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5394-18-3, 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. 5394-18-3 name is 2-(4-Bromobutyl)isoindoline-1,3-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.

General procedure: Chemistry. Compounds 4-10 were synthesized following methodologies previously reported and the analytical and structural data was in agreement with formerly published data.1, 2 Briefly, 4,7-dichloroquinoline or 4-chloropyridine, respectively, was reacted at 100 ºC for 2 to 3 h with 10 molar equivalents (eq) of the respective diaminoalkane to afford the resultant amine; the reaction mixture was then brought to room temperature and diluted with dichlorometane (DCM), and the solution washed with 5% aqueous Na2CO3. The organic layer was isolated and dried over anhydrous Na2SO4, filtered, and the filtrate evaporated to dryness. In the case of the morpholine derivative, 2 eq of morpholine were reacted with 1 eq of 1-(N-phthaloyl)amino-4-bromobutane for 1 day to yield N-(N-phthaloyl)aminobutylmorpholine; after the previously described extraction process, the phthalimide group of the latter compound was removed with hydrazine in ethanol to afford the desired amine. Following, the respective cinnamic acid was activated in N,N-dimethylformamide (DMF), using 2 eq of O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate and 2 eq of N,N-diethyl-N-isopropylamine (DIEA) at 0 oC for 10 min. Subsequently, the corresponding amine was added and the mixture was left to react for 1 day. The mixture was then diluted in DCM, washed with 5% aqueous Na2CO3 and the organic layer collected, dried over Na2SO4, filtered, and the filtrate evaporated to dryness. The crude product was further purified by column liquid chromatography on silica, using a mixture of ethyl acetate and methanol (8:2 v/v) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromobutyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Perez, Bianca C.; Fernandes, Iva; Mateus, Nuno; Teixeira, Catia; Gomes, Paula; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6769 – 6772;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of substituted isatins (1 mmol),cyclic 1,3-diketone (1 mmol), malononitrile (1 mmol)and nano Ag/kaolin (0.085 g, 7 mol%) in EtOH (10mL) was stirred at reflux temperature. Uponcompletion instead of compilation, monitored by TLC(n-hexane/ethyl acetate: 2/1), the reaction mixture wasallowed to cool to room temperature. The catalyst wasseparated by filtration of this solution. The solution wasconcentrated under vacuum to afford the product,which was purified by recrystallization in the ethanol.All the products were identified by comparing of meltingpoint and 1H NMR spectra with those of authenticsamples reported in the literature.2- Amino -5′ – Nitro -2 ‘ , 5- Ioxo -5 , 6 , 7 , 8 -Tetrahydrospiro[Chrom-ene-4,3’-Indoline]-3-Carbonitrile (4c).m.p. 283-285 C; 1H NMR (400 MHz,DMSO-d6) : 1.79 -2.02 (m, 2H, CH2), 2.22-2.26 (m,2H, CH2), 2.62-2.69 (m, 2H, CH2), 7.03 (d, J=8.6Hz, 1H), 7.40 (brs, 2H, NH2), 7.87 (s, 1H, ArH), 8.13(d, J= 6.22 Hz, 1H, ArH), 11.17 (s, 1H, NH).

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sadeghi, Bahareh; Lasemi, Zahra; Azimi, Razieh; Oriental Journal of Chemistry; vol. 31; 2; (2015); p. 1175 – 1179;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, molecular formula is C8H3F2NO2, 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: 774-47-0

Example 3 2-Amino-4,5-difluorobenzoic acid To a 2 liter four neck round bottom flask equipped with a mechanical stirrer, a condenser and a thermometer was charged 100 g of 5,6-difluoroisatin and 900 ml of aqueous 2.5N sodium hydroxide solution. The mixture was stirred until a homogeneous purple solution resulted. To this solution, and with external cooling (acetone/wet ice), was charged 162 ml of a 30% solution of hydrogen peroxide over a period of about 20 minutes. The reaction temperature never rose above 45C throughout the addition. After addition was complete, the reaction mixture was heated for 2 hours and was then cooled to room temperature. This mixture was then carefully quenched into a solution of 6N HCl (200 ml) in a 5 liter flask. The temperature stayed at about 15-20C throughout the addition. A 5 liter flask was used because of extensive foaming during the quench. The pH of the quench mixture was adjusted from about 5.0 to about 1.0 with concentrated hydrochloric acid as precipitation of the product caused stirring to slow down. To the reaction mixture was then added 260 ml of 50% NaOH solution to bring the pH up to 4.50. The mixture was filtered and the solids were sucked dry. The product was then dried in an oven at 40C and reduced pressure to obtain 95 g of the title compound, m.p. 180-181C. NMR(CDCl3 300 MHz): 7.56 (1H,dd,J=8 Hz, J=7 Hz), 6.68 (1H,dd,J=8 Hz, J=7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 774-47-0, its application will become more common.

Reference:
Patent; PFIZER INC.; EP342849; (1990); A3;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem