Tag: M.W=100-200

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

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. 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

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 317-20-4 as follows. 317-20-4

General procedure: To an aqueous mixture of 4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 3a (2 mmol), aldehyde 5 (2 mmol), malononitrile 4 (2 mmol) and piperidine (10 mol %) were added successively at room temperature under an open atmosphere with vigorous stirring. The progress of the reaction was monitored by thin layer chromatography. The precipitated solid was ltered, washed with water (10 mL) and ethanol (5 mL) and then with ether (3 mL). The product was dried under vacuum.

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jayarajan, Ramasamy; Vasuki, Gnanasambandam; Tetrahedron Letters; vol. 53; 24; (2012); p. 3044 – 3048;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2307-00-8

4-(3-Chloro-2-hydroxypropylamino)-N-methylphthalimide Twenty-five grams (g) (0.142 mole) 4-amino-N-methylphthalimide [Flitsch, Chem. Ber. 94:2494(1961)] and 20.7 g (0.21 mole) 1-chloro-2,3-epoxypropane were added to 150 ml 2,2,2-trifluoroethanol and the reaction mixture was heated to reflux with stirring for 48 hours. Seventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation and a heavy yellow precipitate formed when the remaining solution cooled to room temperature. This precipitate was triturated with ethyl acetate, collected by filtration and dried to give 29.5 g (77% yield) of the desired phthalimide intermediate m.p. 136-138.5 C. Analysis: Calculated for C12 H13 ClN2 O3: C, 53.64; H, 4.88; N, 10.45: Found: C, 53.87; H, 4.85; N, 10.81.

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, 2307-00-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Miles Laboratories, Inc.; US4363759; (1982); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1127-59-9 name is 7-Methylindoline-2,3-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. 1127-59-9

General procedure: A solution of isatin derivatives 1 (0.4 mmol), 3-methyl-4-nitro-5-alkenyl-isoxazoles 2 (0.6 mmol) and proline or thioproline or sarcosine (0.8 mmol) in 10.0 mL of CH3CN at 80 ¡ãC for 24 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/EtOAc5:1-3:1) to furnish the corresponding products 3-5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Liu, Xiong-Wei; Yao, Zhen; Yang, Jun; Chen, Zhi-Yong; Liu, Xiong-Li; Zhao, Zhi; Lu, Yi; Zhou, Ying; Cao, Yu; Tetrahedron; vol. 72; 10; (2016); p. 1364 – 1374;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life. 317-20-4

EXAMPLES Example 1 Preparation of 7-Fluoro-1,3-dihydroindol-2-one; To a mixture of 7-fluoro-1H-indole-2,3-dione (100 g, 0.606 mol) in ethylene glycol (500 mL) was added an aqueous hydrazine solution (54% wt, 73 g, 1.21 mol) dropwise over 30 minutes. The mixture was heated to 120 C. and stirred for 6 hours. The mixture was cooled to room temperature and water (500 mL) was added. Concentrated hydrochloric acid (HCl; 60 mL) was added, the mixture was warmed to about 35 to about 40 C., and the mixture was stirred for 1 hour. The mixture was then cooled to about 0 to about 5 C. The solid compound was filtered, washed with cold water and dried at 55 C. under vacuum to give an off-white solid (76 g) in 83% yield with 96% HPLC purity.

The chemical industry reduces the impact on the environment during synthesis 317-20-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2007/27327; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem