Category: 5394-18-3

Adding a certain compound to certain chemical reactions, such as: 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, 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 5394-18-3, Computed Properties of C12H12BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

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:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5394-18-3, 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. 5394-18-3 name is 2-(4-Bromobutyl)isoindoline-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.

General procedure: Chemistry. Compounds 4-10 were synthesized following methodologies previously reported and the analytical and structural data was in agreement with formerly published data.1, 2 Briefly, 4,7-dichloroquinoline or 4-chloropyridine, respectively, was reacted at 100 ºC for 2 to 3 h with 10 molar equivalents (eq) of the respective diaminoalkane to afford the resultant amine; the reaction mixture was then brought to room temperature and diluted with dichlorometane (DCM), and the solution washed with 5% aqueous Na2CO3. The organic layer was isolated and dried over anhydrous Na2SO4, filtered, and the filtrate evaporated to dryness. In the case of the morpholine derivative, 2 eq of morpholine were reacted with 1 eq of 1-(N-phthaloyl)amino-4-bromobutane for 1 day to yield N-(N-phthaloyl)aminobutylmorpholine; after the previously described extraction process, the phthalimide group of the latter compound was removed with hydrazine in ethanol to afford the desired amine. Following, the respective cinnamic acid was activated in N,N-dimethylformamide (DMF), using 2 eq of O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate and 2 eq of N,N-diethyl-N-isopropylamine (DIEA) at 0 oC for 10 min. Subsequently, the corresponding amine was added and the mixture was left to react for 1 day. The mixture was then diluted in DCM, washed with 5% aqueous Na2CO3 and the organic layer collected, dried over Na2SO4, filtered, and the filtrate evaporated to dryness. The crude product was further purified by column liquid chromatography on silica, using a mixture of ethyl acetate and methanol (8:2 v/v) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromobutyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Perez, Bianca C.; Fernandes, Iva; Mateus, Nuno; Teixeira, Catia; Gomes, Paula; Bioorganic and Medicinal Chemistry Letters; vol. 23; 24; (2013); p. 6769 – 6772;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The synthetic route of 2-(4-Bromobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5394-18-3, 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. 5394-18-3 name is 2-(4-Bromobutyl)isoindoline-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.

A^-(4-Bromobutyl)phthalimide 7 (9.70 g, 34.40 mmol) was added to a suspension ofpotassium carbonate (8.20 g, 59.30 mmol) andpiperazine-1-carboxylic acid tert-butyl ester 8(5.00 g, 26.80 mmol) in acetone (125 mL). The mixture was heated at reflux for 14 hours. After cooling to ambient temperature, the reaction mixture was filtered and the filtrate concentrated to a waxy yellow solid. Purification by column chromatography (silica gel, gradient of 70:30 to 0:100 hexanes/ethyl acetate, v/v) gave compound 9 (8.69 g, 84 %) as a yellow solid: *H NMR (300 MHz, CDC13) 8 1.45 (s, 9H), 1.46-1.59 (m, 2H), 1.63-1.76 (m, 2H), 2.32-2.40 (m, 6H), 3.38-3.44 (m, 4H), 3.71 (t, J = 6.9 Hz, 2H), 7.71-7.73 (m, 2H), 7.82-7.84 (m, 2H); ESI MS m/z 388 [C21H29N3O4 + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromobutyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; JOHNSON, Michael, R.; WO2006/23617; (2006); A2;,
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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H12BrNO2

General procedure: Amixture of the corresponding secondary amine 7a-d (5.5 mmol), anhydrous K2CO3 (6 mmol) andcompounds 2-4 (5 mmol) was added inCH3CN (20 ml). The mixture was heated at 65 C for 8-10 h. Thesolvent was evaporated under reduced pressure. Then water (25 mL) was added,and the mixture was extracted with dichloromethane (20 mL × 3). The combinedorganic phases were washed with saturated aqueous NaCl (30 mL), dried oversodium sulfate, and filtered. The solvent was evaporated under a vacuum. The residue was purified on a silicagel chromatography using mixtures of petroleum/acetone as eluent to obtain theoil products 8-10.

According to the analysis of related databases, 5394-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, 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.

N-(4-Bromobutyl)phthalimide (1.5 g, 5.32 mmol) was suspendedin THF (48 mL) and treated with sodium iodide (0.80 g, 5.32 mmol), triethylamine (0.74 mL, 5.32 mmol) and morpholine (0.51 mL, 5.85 mmol). The mixture was then heated at reflux for 16 h. After cooling to ambient temperature, the solvent was removed in vacuo and the residue partitioned between H2O (100 mL) and CHCl3 (100 mL). The aqueous layer was further extracted with CHCl3 (100 mL) and the organic extracts combined, dried (MgSO4), filtered, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica eluting with ethyl acetate to give phthalimide10 (1.02 g, 66%) as a pale yellow oil; numax/cm-12942, 2855, 2807, 1703, 1393, 1359, 1333, 1114, 1069, 1011, 862, 716, 528; deltaH (300 MHz; CDCl3) 7.86-7.77 (2 H, m), 7.73-7.67 (2 H, m), 3.69 (6 H, m), 2.40 (6 H, m), 1.71 (2 H, m), 1.50 (2 H, m); deltaC (75 MHz; CDCl3) 168.5, 134.0, 132.2, 123.3, 66.9, 58.4, 53.7, 37.9, 26.6, 23.8; m/z (+ESI) 289 ([M + H]+, 100); Found: M+, 289.15493. C16H20N2O3 requires 289.15467.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Beinat, Corinne; Reekie, Tristan; Hibbs, David; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 200 – 205;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 26; Compound of Formula VII, Wherein R1 and R2 Taken Together with the Carbon Atom to which they are Attached are CCH2, and R20=(4-Pyridin-3-yl-1H-triazol-1-ylbutyl), Rx=Ac; Step 26a.; To a solution of commercially available 2-(4-bromo-butyl)-isoindole-1,3-dione (7.1 mmol) in DMF (7 ml) was added sodium azide (5 eq.). After stirring at room temperature overnight, the mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed 3 times with water, once with brine, dried over MgSO4, filtered and concentrated under vacuum to give the desired azide product in quantitative yield. 13C NMR (CDCl3, ppm) delta: 168.4, 134.0, 132.1, 123.3, 50.9, 37.3, 26.3, 26.3, 25.9.

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

Reference:
Patent; Or, Yat Sun; Tang, Datong; Gai, Yonghua; Sun, Ying; Xu, Guoyou; Wang, Zhe; US2006/122128; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-bromobutyl)isoindoline-l,3-dione (3.33 g, 11.8 mmol), tert- butyl piperazine-l-carboxylate (2.2 g, 11.8 mmol) and Et3N (4.9 ml, 35.4 mmol) in CH3CN (50 mL) is heated at reflux for 16 h. The mixture is cooled and the solvent is evaporated. The residue is partitioned between EtOAc (70 mL) and water (70 mL). The organic layer is washed with brine (40 mL), dried (Na2S04) and evaporated. The residue is purified by flash column with 1:1 Hexane/EtOAc gives colorless oil (3.91 g, 85%).’HNMR (CDCI3,) delta: 7.83 (dd, 2H), 7,71 (dd, 2H), 3.71 (t, 2H), 3.41 (t, 4H), 2.34- 2.38 (m, 6H), 1.67-1.70 (m, 2H), 1.50-1.56 (m, 2H), 1.45 (s, 9H).LC-MS M+1: 388.12;

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

Reference:
Patent; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; HAN, Bingsong; KUNTZ, Judith D.; LIN, Jian; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZHENG, Xiaozhang; WO2012/154194; (2012); A1;,
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 5394-18-3 as follows. Computed Properties of C12H12BrNO2

N-(4-Bromobutyl)phthalimide (1.95 g, 6.89 mmol) and sodium iodide (81 mg, 0.537 mmol) were added to a suspension Of K2CO3 (1.64 g, 11.88 mmol) and 1-Boc-piperazine (1.00 g, 5.37 mmol) in acetone (25 mL) and refluxed for 22 h. The reaction mixture was filtered and the solid was washed with acetone (3 x 50 mL). The filtrate was concentrated and the residue purified by column chromatography (hexane:EtOAc, 7:3 to 0:1) to afford 2.08 g (100%) of 58. 1H NMR (500 MHz, CDCl3): delta 7.84 (dd, J = 3.0, 5.4 Hz, 2H), 7.71 (dd, J = 3.0, 5.4 Hz, 2H), 3.71 (t, J = 7.1 Hz, 2H), 3.38-3.43 (m, 4H), 2.32-2.40 (m, 6H), 1.70 (m, 2H), 1.53 (m, 2H), 1.45 (s, 9H); MS (m/z): [M+H]+ 388.4.

According to the analysis of related databases, 5394-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; TALDONE, Tony; RODINA, Anna; PATEL, Pallav; KANG, Yanlong; WO2011/22440; (2011); A2;,
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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5394-18-3

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.

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:
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