Tag: M.W=100-200

Electric Literature of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. 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 the title compound as a brown solid.

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

Step 5: 7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) were dissolved in tetrahydrofuran (200 mL). The solution was cooled to -78 C. and n-butyllithium (40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified via Biotage chromatography (Flash40i, silica, 10% then 20% ethyl acetate/hexane) gave 4.1 g (48%) 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. MS (ESI) m/z 180, ([M+H]+).

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2008/153873; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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. COA of Formula: C8H6ClNO

Step 1: 3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one At room temperature, to a solution of 6-chlorooxindole (10.0 g, 59.7 mmol) in t-BuOH (500 mL) and water (2.6 mL) was added pyridinium tribromide (57.25 g, 79 mmol, 3 eq) and the reaction was stirred for 3.5 hr. The reaction was diluted with water (500 mL) and extracted with EtOAc (3*). The combined organic extracts were washed with sat. aq. NaHCO3 (3*), dried over MgSO4, filtered and concentrated to give the title compound as a tan solid (19.66 g, 100% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 325[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 56341-37-8, its application will become more common.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Nitroindolin-2-one

The commercial 5-nitroindolin-2-one (1.00 g, 5.61 mmol) was hydrogenated in EtOH (70 mL) in the presence of 10% Pd-C (315 mg, 2.97 mmol) for 4 h. Then the catalyst was filtered off through Celite, the Celite rinsed with additional EtOH and the solution was evaporated, to give 17 as a brown solid (698 mg, 4.71 mmol, 84% yield). 1H NMR (CD3OD): delta 3.43 (s, 2H, CH2); 6.63-6.65 (m, 2H, Ar); 6.73-6.74 (m, 1H, Ar) ppm. Anal. (C8H8N2O) Calc%: C 64.85, H 5.44, N 18.91; Found%: C 65.03, H 5.49, N 18.83.

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 20870-79-5.

Reference:
Article; Sestito, Simona; Nesi, Giulia; Daniele, Simona; Martelli, Alma; Digiacomo, Maria; Borghini, Alice; Pietra, Daniele; Calderone, Vincenzo; Lapucci, Annalina; Falasca, Marco; Parrella, Paola; Notarangelo, Angelantonio; Breschi, Maria C.; Macchia, Marco; Martini, Claudia; Rapposelli, Simona; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 274 – 288;,
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Electric Literature of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-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 2-amino benzophenone (1 mmol), corresponding isatin or aldehyde (1 mmol) and ammonium acetate (2 mmol) in ethanol (5 mL) was stirred at room temperature. The progress of reaction was monitored by TLC. After completion of the reaction ice-cold water was added and stirred for a while. The solid product obtained was filtered and washed with water. This was further purified by crystallization from ethanol or by short column chromatographyon silica gel using ethyl acetate-petroleum ether as the eluent.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kamal, Ahmed; Babu, Korrapati Suresh; Chandrasekhar, Cheemalamarri; Nagaraju, Burri; Visweswara Sastry; Ganesh Kumar; Tetrahedron Letters; vol. 56; 46; (2015); p. 6373 – 6376;,
Indoline – Wikipedia,
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Related Products of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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-Bromo-2-oxindole 2-Oxindole (1.3 g) in 20 mL acetonitrile was cooled to -10 C. and 2.0 g N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% 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.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6N2O2

EXAMPLE 8 The steps followed in the procedure of this example are illustrated diagrammatically below: STR6 Step (a), Production of 5-Aminophthalide Twenty grams of 4-aminophthalimide was added to a mixture of 41 gm zinc and 122 gm sodium hydroxide in 50 ml water (with good stirring) over 30 minutes. The mixture was stirred another 30 minutes, then heated to 60. When ammonia ceased to be evolved the mixture was heated for an additional 60 minutes, then cooled to about 30. The zinc residues were filtered off and the solution was acidified with 30 ml concentrated hydrochloric acid. The solution was heated to 90 for 45 minutes, then cooled and neutralized with 20 gm solid sodium carbonate, which brought the pH to 8-9. The product was filtered, washed with water and air dried. Wt=16.8 gm, m.p.=177-189.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pennwalt Corporation; US4665181; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Computed Properties of C8H9N

Intermediate 5A 2-(4-bromo-3-fluorophenyl)-1-(isoindolin-2-yl)ethanone [0492] [0493] To a mixture of 2-(4-bromo-3-fluorophenyl)acetic acid (300 mg, 1.287 mmol), isoindoline (0.161 mL, 1.416 mmol), and HATU (734 mg, 1.931 mmol) in DMF (5 mL), was add DIEA (0.450 mL, 2.6 mmol). The mixture was stirred rt for 18 h. The reaction mixture was diluted with EtOAc, then was washed with H2O, 1N HCl, H2O, sat. Na2CO3 and brine. The organic phase was dried (Na2SO4), filtered through a 1? pad of SiO2 and concentrated. The crude product was purified by flash chromatography (gradient from 0 to 100% ethyl acetate/hexanes) to afford 379 mg (88%) of Intermediate 5A as an off-white solid. MS (ESI) m/z: 333.9 (M+H)+; 1H NMR (400 MHz, CDCl3) delta 7.50 (dd, J=8.0, 7.4 Hz, 1H), 7.33-7.22 (m, 4H), 7.14 (dd, J=9.2, 2.0 Hz, 1H), 7.01 (dd, J=8.5, 1.9 Hz, 1H), 4.83 (s, 4H), 3.72 (s, 2H)

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

Reference:
Patent; Glunz, Peter W.; Zou, Yan; Quan, Mimi L.; US2014/206686; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.55 2-((2-(2-(Pentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (3C) White powder, mp 125-126 C, 84% yield; 1H NMR (400 MHz, CDCl3): delta 0.92-0.95 (t, 3H, CH3), 1.59-1.61 (m, 2H, CH2), 1.93 (s, 3H, CH3), 2.23-2.27 (t, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.75-7.76 (m, 2H, Ar), 7.86-7.87 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 13.8, 14.0, 17.5, 19.6, 19.8, 22.9, 32.2, 34.1, 40.6, 45.0, 45.1, 123.6, 131.7, 134.3, 158.0, 166.7, 170.0, 171.1.

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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Indoline | C8H9N – PubChem

Related Products of 5428-09-1, 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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

The chemical industry reduces the impact on the environment during synthesis 2-Allylisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem