Category: indolines-derivatives

Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50¡ãC for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 ¡Á 30 mL) and cold aqueous ethanol (2 ¡Á 1 mL) to afford pure product 4.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 7-Fluoro-1-methylindoline-2,3-dione

Add beta-bromocycloalkenyl formaldehyde (131.2 mg, 0.75 mmol), N-methyl-7-fluoroisatin (89.6 mg, 0.5 mmol), thiazole salt (18.6 mg, 0.05 mmol) to a dry Schlenk tube. , Cesium carbonate (162.9 mg, 0.5 mmol), dioxane (5 mL), and heated under reflux for 12 hours. After the reaction was completed, the reaction solution was cooled and the solvent was removed by rotary evaporation. The product was separated by silica gel column chromatography (petroleum ether / ethyl acetate = 4/1) to obtain 100.0 mg of the product as a pale yellow solid with a yield of 73%.

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Institute of Technology; Wang Gang; Wu Jiang; Cheng Xing; He Zhaolin; Yuan Xiangfu; Xi Jiangbo; (9 pag.)CN110698490; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; WO2014/140078; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 105310-75-6, name is cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide, molecular formula is C23H24N2O3, 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. Product Details of 105310-75-6

In a round bottom flask, 450ml of 40% aqueous methylamine solution was charged and 1 OOg of compound of formula III, prepared as in Example 1 , was added at about room temperature. Then the temperature was raised to about 40C to about 45C and stirred for about 2h. The reaction mixture was cooled to about room temperature and 700ml of toluene was added and stirred for about 30min. The layers were separated and the aqueous layer was extracted twice with each 200ml of toluene. The organic layers were combined and washed with 200ml of water followed by washing with 100ml of 20% aqueous sodium chloride solution. The organic layer was distilled out under reduced pressure at about 50C to about 55C, until substantially all of the solvent was distilled out. The crude was cooled to about room temperature and 350ml of ethyl acetate was added and stirred the contents for about 15min. Then 5g of activated charcoal (5g of charcoal in 50ml of isopropanol) was added to the solution and stirred for about 30min at about room temperature. The solution was filtered through Hyflo bed and the Hyflo bed was washed with 50ml of ethylacetate. The solution was cooled to about 20C and 93g of 12% w/w hydrogen chloride solution in ethylacetate was added at about 20C to about 25C over a period of about 30min and the contents were stirred for about 2h at about 20C to about 25C. The precipitated product was filtered and washed with 100ml of ethylacetate. The product was dried at about 55C to about 60C under vacuum for about 6h to yield 50g of milnacipran hydrochloride.Purity by HPLC: 99.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105310-75-6, its application will become more common.

Reference:
Patent; GLENMARK GENERICS LIMITED; JAMBUKAR, Nagambar Genuji; GHARPURE, Milind; SINARE, Sudam Nanabhau; THOMBRE, Pravin Chhaburao; KHAN, Mubeen Ahmed; WO2011/158249; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5, 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. 3676-85-5 name is 5-Aminoisoindoline-1,3-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.

Example 76 N-Cyclohexylmethyl-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (232 mg, 0.85 mmol, 1.2 eq) and triethylamine (85 mg, 0.85 mmol, 1.2 eq) were added to a solution of cyclohexylacetic acid (100 mg, 0.70 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (114 mg, 0.70 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 150 min. After the completion of the reaction, the reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by a preparative TLC [chloroform-acetone] to give the title compound as a crystal (46 mg, 21.7%). MS m/z: 301 1H-NMR delta: 0.85 – 0.96 (2H, m), 1.07 – 1.26 (3H, m), 1.35 – 1.47 (1H, m), 1.58 – 1.73 (5H, m), 2.97 (2H, t, J = 6.22 Hz), 6.42 (1H, t, J = 5.73 Hz), 7.56 (1H, dd, J = 1.95, 8.29 Hz), 7.66 (1H, d, J = 8.30 Hz), 8.01 (1H, d, J = 1.71 Hz), 9.11 (1H, s), 11.06 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 85342-65-0, 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. 85342-65-0, name is 4,5,6,7-Tetrachloro-2-hydroxyisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A screw-capped culture tube with a stir bar was charged with alkyl carboxylic acid (0.2 mmol), /V-hydroxyphthalimide or tetrachloro-/V-hydroxyphthalimide (0.2 mmol, 1 .0 equiv) and Lambda/,Lambda/’-dicyclohexylcarbodiimide (0.2 mmol, 1 .0 equiv). The tube was then evacuated and backfilled with argon for three times. CH2CI2 (2.0 mL) was added and the resulting mixture was stirred at room temperature for 2 h before the volatiles were removed in vacuo. MgBr2 – OEt2 (77 mg, 0.3 mmol, 1 .5 equiv) was added. The tube was evacuated and backfilled with argon for three times. Suspension A (0.8 mL, NiCI2 – 6H20 (10 mol%)/L1 (13 mol%) in THF) or suspension C (0.8 mL, NiCI2 – 6H20 (10 mol%)/L2 (13 mol%) was added. The mixture was stirred vigorously at room temperature for 15 min (or until no granular MgBr2 OEt2 was observed) and was subsequently cooled to 0 C before a suspension of [B2pin2Me]Li in THF (1 .1 mL) was added in one portion (note: do not add it dropwise). After being strred for 1 h, the reaction was warmed to room temperature and stirred for another 1 h. The reaction mixture was then quenched with 0.1 N HCI (10 mL) and extracted with Et20 (5 mLx2). The combined organic layers were dried over Na2S04, concentrated in vacuo and purified by column chromatography to give the desired product.

The chemical industry reduces the impact on the environment during synthesis 4,5,6,7-Tetrachloro-2-hydroxyisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BARAN, Phil; LI, Chao; WANG, Jie; CHATTERJEE, Arnab, Kumar; KUMAR, Manoj; YU, Shan; JOHNSON, Kristen, Ann; QIN, Tian; SHANG, Ming; (167 pag.)WO2018/175173; (2018); 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 118289-55-7

EXAMPLE 3; 5-(2-(4-Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride. (I); A reactor is loaded with 131 g (0.57 mol) of 6-chloro-5-(2-chloro-ethyl)-1,3-dihydro-indol-2-one, 125 g (0.57 mol) of piperazinyl benzoisothiazole, 260 ml of dimethylsulfoxide, 26 ml of water and 4.3 g (0.0285 mols) of Nal. The reaction mixture is added with 103 g (0.969 mol) of Na2CO3, with stirring under nitrogen atmosphere. The resulting mixture is heated to about 115-125 C. in 1 h and kept at said temperature under stirring for approx. 1 hr 45 min, then cooled and slowly added in about 25 min with isopropyl alcohol (650 ml), at a temperature of about 110 C., then slowly cooled at 25 C. The filtrate and the precipitate are washed with isopropyl alcohol (2¡Á130 ml) to obtain 310 g of 5-(2-(4-benzo[d]isothiazol-3-yl) piperazin- 1-yl)ethyl)-6-chloro- 1,3-dihydro-2H-indol-2-one free base, as a crystalline solid. The resulting product is placed in a 3 L beaker with 1500 ml of purified water, and 150 ml of 32% HCl are dropped therein with stirring. The reaction mixture is kept under stirring for 10 min, filtered, washed with purified water (2¡Á500), dried to give 260 g of 5-(2-(4-benzo[d]isothiazol-3-yl) piperazin- 1-yl)ethyl)-6-chloro- 1,3-dihydro-2H-indol-2-one hydrochloride, as a crystalline solid.

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIPHARMA S. P. A.; LUNDBECK PHARMACEUTICALS ITALY S. P. A.; US2007/117810; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1677-48-1, These common heterocyclic compound, 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione, 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.

5,6-Dichloro-7-nitroisatin (13i) was obtained in 51% yield from 5,6-dichloroisatin (13g) by using a similar procedure as that for 13h. Mp 200-201 C.; IR: 1784, 1759, 1743, 1626, 1547, 1442, 1332 cm-1; 1 H NMR delta 11.934 (s, 1H), 8.125 (s, 1H); HRMS Calcd for C8 H2 Cl2 N2 O4: 259.9391; Found: 259.9384.

The synthetic route of 1677-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; State of Oregon, Acting by and through the Oregon State Board of Higher Education, Acting for and on Behalf of the Oregon Health Sciences University and the University of Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5597922; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, 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 239463-85-5, Recommanded Product: (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

3- {5 – [(2R) -2-aminopropyl] -7-cyano-2,3-dihydro -1H- indol-1-yl} propyl benzoate (2R, 3R) – mono tartrate 50g(97.5mmol, 1eq ) was poured into methanol 500ml, potassium hydroxide 12g (214mmol, 2.2eq)was reflux for 2 hours stirring was charged. After completion of the reaction, after cooling to room temperature filtered, the filtrate was concentrated (R)-5-(2-aminopropyl) -1- (3-hydroxypropyl) indoline-7-carbonitrile 25 g (100%) It was obtained.

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, (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyongbo Pharm Company Limited; Son, Feju; Ban, Sonfun; Kwon, Hyok Bom; Yoon, Ik Hwan; Choi, Min-sik; Yang, Jiwon; (15 pag.)JP2016/23186; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 446292-08-6, These common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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.

100 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I), 1000 ml methanol and 119 g methyl amine were added to RBF at 25 C. to 35 C. The reaction was heated to 60 C. to 65 C. for 1-2 hours. To the reaction mass succinic acid (15 g) was added till to pH 5.5 to 6.0 and maintained for 30 minutes. The reaction mass was cooled to 45 to 50 C. and maintained for 30 minutes. The reaction mass was cooled to 25 to 35 C. and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml*2) afforded succinate salt of (S)-4-(4-(5-(aminomethyl)-2-oxo-oxazolidin-3-yl)phenyl)morpholin-3-one of Formula (JS).

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem