Month: April 2021

Synthetic Route of 480-91-1, The chemical industry reduces the impact on the environment during synthesis 480-91-1, name is Isoindolin-1-one, I believe this compound will play a more active role in future production and life.

Phthalimidine (800 mg, 6.01 mmol) was dissolved in THF(40 mL). At ambient temperature triethylamine (670 mg,6.62 mmol) was added dropwise and the mixture was stirred for5 min, whereupon dichlorophenylphosphine (538 mg, 3.01 mmol)was added and the mixture was stirred for one day. Thereafter thewhite precipitate was filtered and washed with THF (3 mL). Thecombined filtrate and washings were evaporated to dryness (condensationof volatiles into a cold trap under reduced pressure), theresidue was dissolved in THF (10 mL) and the solution was filteredthrough Celite. After vapor diffusion of n-pentane into the filtrate(for one week), white crystalline product suitable for single-crystalX-ray diffraction was obtained. The supernatant was removed bydecantation, the white solid was washed with n-pentane (3 mL)and dried in vacuo to yield 480 mg (1.29 mmol, 43%) of 1b.

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

Reference:
Article; Gericke, Robert; Wagler, Joerg; Polyhedron; vol. 125; (2017); p. 57 – 67;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3, A common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

5-Nitro-2-oxindole 2-Oxindole (6.5 g) was dissolved in 25 mL concentrated sulfuric acid and the mixture maintained at -10 to -15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice-water. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid. The crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Pharmacia Corporation; US2003/216410; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;; ; Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-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.

We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid. Mp: 177.0-178.1 C. 1H NMR (400 MHz, DMSO-d6): delta = 8.00 (1H, m), 7.86 (1H, s), 7.26 (4H, m), 6.70 (1H, d, J = 8.94 Hz), 5.71 (1H, s), 3.81 (1H, m), 3.21 (1H, m), 3.00 (2H, m), 2.32 (3H, s); 13C NMR (400 MHz, DMSO-d6): delta = 171.16, 156.59, 137.70, 137.38, 131.42, 130.49, 129.23, 128.83, 126.02, 120.28, 104.61, 61.16, 49.18, 26.15, 20.68 ppm. Calculated for C17H16N2O4, MS (ESI): m/z = 313.1181 (M+H)+.

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

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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 496-12-8 as follows.

A 1.0 g (8.4 mmol) amount of isoindoline was dissolved in 25 mL of acetonitrile. After addition of potassium carbonate (2.3 g, 16.8 mmol), the resulting mixture was heated at 70 C. After 30 min, the solution was allowed to cool to room temperature. A 4.2 mL (47.2 mmol) amount of 1-bromo-3-chloropropane was added and the reaction mixture stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3¡Á30 mL dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled collection of the product as a brown liquid (1.27 g, 77%). TLC: Rf 0.7 (DCM:MeOH(NH3), 9:1, v/v). 1H NMR (300MHz, CDCl3) delta: 7.21 (s, 4H, Haro); 3.95 (s, 4H, 2 CH2); 3.69 (t, 3J=7Hz, 2H, CH2); 2.90 (t, 3J=7Hz, 2H, CH2); 2.07 (p, 3J=7Hz, 2H, CH2). 13C NMR (75MHz, CDCl3) delta: 140.0 (2Caro); 126.7 (2Caro); 122.3 (2Caro); 59.1 (2CH2); 53.0 (CH2); 43.1 (CH2); 31.9 (CH2). LCMS (ESI+): Calc. for [M+H]: 196.05; 198.07. Found: 195.95; 197.91.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, 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 1168150-46-6, Computed Properties of C18H15NO4

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

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, (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 6941-75-9 as follows. SDS of cas: 6941-75-9

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22120-50-9, name is 2,3-Dimethylindoline, 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 22120-50-9, Safety of 2,3-Dimethylindoline

A mixture of 2,3-dimethylindoline (0.10 g, 0.679 mmol) and 2-bromoethanamine hydrobromide(0.153 g, 0.747 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purifiedby preparative HPLC to give the title compound as a mixture of cis and trans ismoers that was notpurified further (128 mg). LCMS m/z = 191.2 [M+H]+.

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

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

Reference of 56341-37-8, These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

Preparation of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl] ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one: (i) Preparation of 6-chloro-5-(chloroacetyl)oxindole : charge 250 ml of methylene dichloride and 100 gm of 6-chloro-oxindole in a 3 litre three neck flask under nitrogen atmosphere at 25 to 30C. Cool gradually to 0 to 5C under stirring and charge 199 gm of anhydrous aluminium chloride in portions at 0 to [50c] and stir for 15 min at 0 to 5C. Add 87.6 gm of chloroacetyl chloride slowly at 0 to 5C over 30 mins. Stir at 0 to 5C for 30 mins. Heat the reaction mixture slowly to reflux (40 to 45C)] over 30 mins. Reflux for 12 hrs. On completion of reaction cool the reaction mixture to 25 to 30C, pour into 1 kg ice, 50 ml of conc. HCl and 450 ml of demin water at 0 to 10C under stirring over 30 mins. Stir for 30 mins, filter solid product and wash with demin water. Prepare a slurry of the solids in hexane and suck dry the product. Dry the product at 70 to 75C.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2003/99198; (2003); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 334952-09-9 as follows. category: indolines-derivatives

Example 39 COMPOUND IN-031 3-[5-(2-Morpholin-4-yl-ethoxy)-1H-indol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 5-(2-morpholin-4-yl-ethoxy)-1HH-indole-2-carbaldehyde to give the title compound.

According to the analysis of related databases, 334952-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); A1;,
Indoline – Wikipedia,
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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 7699-18-5

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used 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:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem