Month: August 2021

Related Products of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
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. 56341-39-0, name is 6-Fluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6FNO

PREPARATION 3 1-(3-Chloropropionyl)-6-fluoroindoline This provides an alternative method of preparing the title compound, whose preparation is also described in Example 1(6). 424 ml (3.35 mol) of a boron trifluoride-diethyl ether complex were added dropwise at 0 C. over a period of 40 minutes to 1.5 liters of a suspension of 106 g (2.52 mol) of sodium borohydride (purity 90%) in tetrahydrofuran, and the mixture was stirred at room temperature for 1 hour. At the end of this time, 194 g (1.28 mol) of 6-fluorooxindole was added at 0 C. to the reaction mixture, and the mixture was heated under reflux for 84 hours. The reaction mixture was then cooled to 0 C., after which 1 liter of 6N aqueous hydrochloric acid was added dropwise over a period of 30 minutes. The resulting mixture was heated under reflux for 2 hours, after which it was concentrated by distillation at atmospheric pressure until the volume of the reaction mixture was reduced to about 1 liter. About 400 g of sodium hydroxide was added to the reaction mixture at 0 C. over a period of 1 hour to adjust the pH to a value of at least 14, and then the mixture was filtered. The filtrate was extracted with 1 liter of ethyl acetate and the organic extract was dried over anhydrous sodium sulfate. The mixture was filtered, and then the solvent was removed from the filtrate by distillation under reduced pressure to obtain 370 g of a crude product containing 6-fluoroindoline. This crude product was dissolved in 1 liter of acetone, and 125 ml of 3-chloropropionyl chloride was added dropwise to the resulting solution at 0 C. over a period of 50 minutes, after which the mixture was heated under reflux for 40 minutes. The reaction mixture was then cooled to room temperature and concentrated by evaporation under reduced pressure until the volume of the mixture was reduced to about 400 ml. 500 ml of water and 100 ml of acetone were added to the reaction mixture, and the precipitated crystals were collected by filtration. The crystals were washed with water and then air-dried. The crystals thus obtained were washed with a 2:3 by volume mixture of ethyl acetate and hexane and then with hexane and dried to obtain 158 g (yield: 54%) of the title compound as pale yellow crystals.

According to the analysis of related databases, 56341-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; US5773618; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

General procedure: Compounds 4-9 were prepared through knoevenagel condensation of compounds 12 and 13 (1 mmol) with active methylene compounds including 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one, oxindole and indolinone (1 mmol). The reactants were heated at 160-180 C for about 10-20 min in oil bath and the completion of the reaction was monitored using TLC. The crude products were solidified by triturating with diethyl ether and purified by recrystallization and column chromatography.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Palwinder; Shaveta; Sharma, Surbhi; Bhatti, Rajbir; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 77 – 82;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-31-7, The chemical industry reduces the impact on the environment during synthesis 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

190gms(0.7755mole) 4-phthalimido cyclohexanol are dissolve in 1480ml chloroform.Add solution of H2SO4 (435.87gm, 4.4476mole cone. H2SO4 was added in 900 mlwater). Cool mass to 25C,add lot wise 180.5gm(0.6139mole) potassium dichromate inone hour. Stir mass for three hours, add 900 ml water and separate organic phase.Organic phase was washed with water and 2% NaHCO3 solution, after drying andconcentration of extracts product was isolated by adding methanol and water mixture.YIELD: 175g(92.4%)PURITY: 96.01%.

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-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 13220-46-7, 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. 13220-46-7, name is 4-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-Methyl-oxindole was condensed with 3-(2-formyl-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrol-3-yl)-propionic acid and piperidine in ethanol to give the title compound. MS (m/z) 365 [M+1].

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

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

Synthetic Route of 24566-79-8, The chemical industry reduces the impact on the environment during synthesis 24566-79-8, name is N-(6-Bromohexyl)phthalimide, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

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, N-(6-Bromohexyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20780-72-7,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.

A mixture of 1.0 g (4.4 mmol) of 4-bromoindole diketone,Methyl acrylate (0.46 g, 5.3 mmol)PdCl2 (PPh3) 20.15 g (0.22 mmol),K3PO41.6 g (6.2 mmol),Into the microwave reaction flask,Add 5 mL of DMF,Argon protection,And reacted at 145 ° C for 30 min in a microwave reactor.TLC detection reaction is complete,The reaction solution was washed three times with 100 mL of saturated brine,Extracted with dichloromethane,Combined organic phase,Dried over anhydrous sodium sulfate and purified by silica gel column chromatography using developing solvent petroleum ether: ethyl acetate = 5: 1-1: 1,200-300 mesh,4-methyl acrylate indole diketone 0.65 g, yield 64percent.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (8 pag.)CN104370799; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, 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. category: indolines-derivatives

Reference Example 23 4,6-Dichloro-3-hydroxy-3-(2-naphthyl)oxindole To a solution of 2-bromonaphthalene (2.952 g) in anhydrous THF (25 mL) was added portion wise a solution of n-butyl lithium in n-hexane (1.55 N, 10.12 mL) at -78 C. The reaction solution was stirred for 30 minutes. To the mixture was then added portion wise a solution of 4,6-dichloroisatin (1.54 g) in anhydrous THF (25 ml) for 50 minutes. The reaction mixture was stirred for 2 hours. Then the mixture was allowed to warm to room temperature. To the mixture was added 1N HCl and extracted by ethyl acetate. The organic phase was separated, washed with 1N HCl and brine and dried over MgSO4 and concentrated. Purification was carried out by silica gel chromatography (hexane:ethyl acetate, 2:1 to 1:1 gradient) to give the title compound (0.652 g, yield: 27%). 1H NMR (DMSO-d6, 300 MHz) delta 6.93 (1H, s), 6.96 (1H, d, J=1.7 Hz), 7.12 (1H, d, J=1.7 Hz), 7.23 (1H, m), 7.49 (2H, m), 7.80-7.94 (4H, m), 10.80 (1H, brs).

The synthetic route of 4,6-Dichloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Co., Ltd.; US6576656; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 954-81-4, 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. 954-81-4 name is N-(5-Bromopentyl)phthalimide, 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.

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%).?HNMR (400 IVIFIz, CDC13): 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (340 pag.)WO2018/98207; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Prepared using method described in Example 4, step (a) with the solution being initially irradiated for 90 min and then a further 90 min using 5-cyclopropyl-6-methyl-7-(tetramethyl- 1 ,3,2-dioxaborolan-2yl)-oxazolo[4,5-c]quinolin-4-one (Intermediate D) and 5-bromo-2,3- dihydro-1 H-isoindol-1-one. Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1 , 1 ‘- biphenyl)[2-(2’-amino-1 , 1 ‘-biphenyl)]palladium(ll) (10% mmol) was used as catalyst and .2- dicyclohexylphosphino-2′,4′,6’-triisopropylbiphenyl (10% mmol) as ligand. Column chromatography was carried out, eluting with 0-20% MeOH in DCM. 1 H NMR (Method A) (CDCb): delta ppm 8.10 (s, 1 H), 7.99 (d, J = 7.8 Hz, 1 H), 7.81 (d, J = 7.9 Hz, 1 H), 7.53 (d, J = 8.0 Hz, 1 H) 7.50 (s, 1 H), 7.28 (s, 1 H), 6.22 (s, 1 H), 4.56 (s, 2H), 3.69- 3.61 (m, 1 H), 2.54 (s, 3H), 1.33 (d, J = 6.8 Hz, 2H) 0.74 – 0.66 (m, 2H); LC-MS (Method D) 372.0 [M+H]+; RT 1.96 min

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; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem