Author: tianli

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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 99365-40-9

Pottasium tert-butoxide (0.085 g, 0.8 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (4.00 mL, 44.4 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.0 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85 C for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid. LRMS (m/z): 292/294 (M-1)-. 1H-NMR delta (DMSO-d6): 1.99-2.08 (m, 2H), 2.13-2.22 (m, 2H), 2.41-2.50 (m, 2H), 2.82-2.92 (m, 2H), 7.07 (d, J=3.0 Hz, 1 H), 7.21 (dd, J=9.0 and 3.0 Hz, 1 H), 7.50 (d, J=9.0 Hz, 1 H), 10.70 (brs, 1H).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, name is Indolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 59-48-3

EXAMPLE 17 3-[5-(5-Ethyl-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-Acetyl-2-oxindole as a brown solid.

Statistics shows that 59-48-3 is playing an increasingly important role. we look forward to future research findings about Indolin-2-one.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., 3416-57-7

(Synthesis of Intermediate 3)102 g (0.5 mol) of the intermediate 1 and 147 g (0.5 mol) of the intermediate 2 thus obtained were mixed with 500 ml of ethanol, and the mixture was stirred while cooled to 5 C. to 10 C. 201 ml of SM-28 (28% sodium methoxide methanol solution) was added dropwise to the dispersion. The temperature of the reaction solution was kept to 10 C. or lower. After dropwise addition, the mixture was allowed to warm to room temperature and stirred additionally for 30 minutes, and then, after addition of 20 ml of water, stirred as heated under reflux additionally for 4 hours. After reaction, the reaction solution was cooled to room temperature, and 750 ml of water was added dropwise, allowing precipitation of the crystal. The crystal was filtered, washed with water and dried. The crystal was washed ad dispersed and stirred in 1,000 ml of n-hexane, filtered and dried, to give 143 g of an intermediate 3 (yield: 82.2%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; FUJIFILM CORPORATION; US2012/238752; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

To a solution of 6-bromo-4-chlorobenzo[c][1,2,5]oxadiazole (372 mg, 1.6 mmol) in NMP (3 mL) in a 4 dram vial was added isoindoline (238 mg, 2 mmol) and triethylamine (400 muL, 2.9 mmol). A cap was tightly fitted and the reaction was heated at 85 C. O/N. The reaction was worked up by diluting with EtOAc (60 mL) and washing with 1M HCl (3*20 mL) and brine (1*20 mL). The organic phase was dried with MgSO4 filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 Hex/EtOAc) to give 208 mg (41% yield) of 6-bromo-4-(isoindolin-2-yl)benzo[c][1,2,5]oxadiazole. 1H NMR (300 MHz, CDCl3) delta=7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H).

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 496-12-8.

Reference:
Patent; Treventis Corporation; Reed, Mark A.; Wood, Thomas K.; Banfield, Scott C.; Barden, Christopher J.; Yadav, Arun; Lu, Erhu; Wu, Fan; (204 pag.)US2017/174641; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 59-48-3.

2-Oxindole (5.3 g, 0.04 mol) was suspended in 64 mL of acetonitrile cooled in a ice bath. N-Bromosuccinimide (7.5 g, 0.042 mol) was slowly added with vigorous stirring keeping the temperature below 12 C. The mixture was stirred for 1 hour at 10 C. and then for 1 hour while warming to room temperature. The precipitate was collected by vacuum filtration, washed with 8 mL of ethanol and slurry-washed in 140 mL of refluxing ethanol to give 5.8 g (68% yield) of the title compound.

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

Reference:
Patent; SUGEN, Inc.; US2004/186160; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Triethylamine (0.33 ml, 2.37 mmol) and isoindoline (0.27 ml, 2.38 mmol) were added in turn to a solution of methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (820 mg, 2.25 mmol) in dimethyl sulfoxide (5 ml) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and ice water (50 ml) was added thereto. The mixture was stirred and the precipitates were filtered, washed with water and dried. The resultant yellow crystals were purified by column chromatography on silica gel (n-hexane/ethyl acetate = 15) to give methyl ester of 5-chloro-2-(1,2,3,4-tetrahydroisoquinolinio)-3-nitrobenzoic acid (608 mg, 81 %) as yellow crystals. m.p.: 114 – 115 C; IR (Nujol): 1743, 1705, 1603, 1589, 1529, 1503 cm-1; APCI-MS m/z: 333[M+H]+.

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 496-12-8.

Reference:
Patent; Endo, Hitoshi; EP1481965; (2004); A1;,
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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 923590-95-8

Step 1: preparation of benzyl 4-bromoisoindoline-2-carboxylate (compound 3a) To a solution of 4-bromoisoindoline hydrochloride (235 mg, 1.0 mmol) in THF (4 mL) was added TEA (355 mg, 0.49 mL, 3.5 mmol). The mixture was then cooled with ice-water bath. CbzCl (256 mg, 0.22 mL, 1.5 mmol) was added dropwise. The reaction mixture was stirred at rt overnight, then diluted with water (20 mL), and extracted with EtOAc (30 mL) twice. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to afford compound 3a (255 mg) as a pink solid. MS: calc’d 332&334 (MH+), measured 332&334 (MH+).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. Hoffmann-La Roche AG; The designation of the inventor has not yet been filed; (99 pag.)EP3623369; (2020); A1;,
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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 59-48-3

PREPARATION 14 5-Acetyl-2-oxindole To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225-227 C.

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

Reference:
Patent; Pfizer Inc.; US4721712; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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.

N-Nitrosoisoindoline 18: To a solution of isoindoline 45 in a mixture of 10 mL of acetic acid and 20 mL of water, an aqueous solution of NaNO2 (1.53 g, 22.2 mmol) in 10 mL of water was added at 0 C. The whole was stirred for 2 h, then extracted with CH2Cl2, and the organic layer was washed with 2 N aqueous NaOH, 0.5 N aqueous HCl, brine, and dried over sodium sulfate. The solvent was evaporated to give a residue, which was chromatographed (hexane: AcOEt = 1: 4 to 1: 3) to give 18 as an oil (1.32 g, 8.91 mmol, 45% from alpha,alpha-dibromo-o-xylene). Mp: 85-89 C (recrystallized from MeOH, grayish needles). MS ([M+H]+): 149. 1H NMR (400 MHz, CDCl3): delta 7.40-7.31 (4H, m), 5.63 (2H, s), 4.90 (2H, s).

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 496-12-8.

Reference:
Article; Ohwada, Tomohiko; Ishikawa, Satoko; Mine, Yusuke; Inami, Keiko; Yanagimoto, Takahiro; Karaki, Fumika; Kabasawa, Yoji; Otani, Yuko; Mochizuki, Masataka; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2726 – 2741;,
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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., 446292-07-5

300 ml of THF were added to 20 g of 2-((2i?)-2-hydroxy-3-{ [4-(3-oxomorpholin-4- yl)phenyl]amino}propyl)- lH-isoindol-l ,3(2H)-dione (14, 0.0506 mol), 16 g of Iota , Gamma- carbonyldiimidazole (0.09869 mol) and 0.1 g of 4-dimethylamino)pyridine. The suspension was stirred and heated to boiling for 7 hours, then slightly cooled and another portion of Iota , Gamma-carbonyldiimidazole (0,09869 mol) was added. Then, the suspension was stirred under boiling for 14 hours. After that the mixture was cooled to 25C, which was followed by filtration, washing of the cake with THF, with an ethanol/water mixture (9: 1) and drying. 15.6kg of an off-white powder was obtained that melted at the temperature of 216 to 217C; HPLC 99.9%, content of the (R)- isomer below 0.03%, yield 73%.

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; ZENTIVA, K.S.; HALAMA, Ales; KRULIS, Radim; BRICHAC, Jiri; WO2013/120464; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem