Category: 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., SDS of cas: 5394-18-3

To a solution of N-(4-bromobutyl)phthalimide (8g, 0.03mol) in ethanol (50ml) was added morpholine (2.97ml, 0.034mol) and triethylamine (7.9ml, 0.06mol). The reaction was then refluxed under N2 atmosphere for 2Oh after which LC-MS indicated the clean formation of 2- [4-(4-morpholinyl)butyl]-1 H-isoindole-1 ,3(2H)-dione. The reaction mixture was cooled to ambient temperature followed by the addition of hydrazine hydrate (3.26ml, 0.057mol). The reaction mixture was brought up for reflux again for 30min during which a white precipitate was formed. The reaction mixture was cooled to room temperature before the white precipitate was filtered and the filtrate passed through an SCX column (eluting with 100% methanol followed by 10% 2M ammonia in methanol) to afford 4-(4-morpholinyl)butyl]amine (1.8g, 41%).; 4-(4-Morpholinyl)butyl]amineA solution of morpholine (3ml, 34.9mmol), N-(4-bromobutyl)phthalimide (8g, 29mmol) and triethylamine (8ml, 58mmol) in ethanol (55ml) was refluxed for 16h, by which the LC-MS showed reaction completion. The reaction was cooled to room temperature. Ethanol (10ml) and hydrazine hydrate (6ml, 58mmol) were added and the mixture refluxed for 20min, by which a white solid crashed out. The reaction was filtered and the filtrate passed through SCX with methanol followed by 10% 2M ammonium hydroxide in methanol. The latter fractions eluted with 10% ammonium hydroxide in methanol were combined and concentrated in vacuo to afford a bright yellow oil (3g). ELSD LC-MS, (MH+=I 59).

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; GLAXO GROUP LIMITED; WO2009/71577; (2009); A1;,
Indoline – Wikipedia,
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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., Formula: C12H12BrNO2

General procedure: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

The synthetic route of 5394-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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: N-(4-mercaptobutyl) phthalimide (3) : N-(4-bromobutyl)-phthalimide (2, 2.81 g, 10 mmol) was dissolved in DMF (30mL) at room temperature. Sodium hydrosulfide (0.62 g, 11mmol) and TBAB (0.98 g) was added and stirred at room temperature under N2 atmosphere for 10 h. After the completionof the reaction (monitored by TLC analysis), the mixture was diluted with water and extracted with ethyl acetate (3×40 mL). The organic layer was washed twice with saturated brine (2×40 mL), dried over anhydrous sodium sulfateand the solvent was evaporated to dryness. The crude residue was purified by chromatography on silica (ethyl acetate/petroleum ether = 1/20) to afford pure 3 (2.00 g, 85% yield) as wax. 1H NMR (CDCl3, 400 MHz), delta: 1.44 (t, 1H, J=8.0Hz, S16H), 1.63-1.70 (m, 2H, C13H), 1.76-1.84 (m, 2H,C14H), 2.57 (q, 2H, C15H), 3.68 (t, 2H, J=6.9 Hz, C12H),7.72-7.82 (m, 4H, PhH); 13C NMR (CDCl3, 100 MHz), delta:24.0 (C15), 27.2 (C13), 31.0 (14), 37.1 (C12), 123.0 (C3,C6), 131.9 (C4, C5), 133.8 (C1, C2), 168.0 (C7, C9). (KunHu [17]: 1 H NMR (CDCl3, 500 MHz), delta: 1.26 (t, 1H, J = 7.0Hz), 1.63-1.69 (m, 2H), 1.77-1.83 (m, 2H), 2.55-2.59 (dd,2H, J = 7.0 Hz), 3.70 (t, 2H, J = 7.0 Hz), 7.72 (dd, 2H, J =3.0, 5.5 Hz), 7.84 (dd, 2H, J = 3.0, 5.5 Hz); 13C NMR(CDCl3, 125 MHz), delta: 24.09, 27.31, 31.10, 37.33, 123.24,132.11, 133.95, 168.39).

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:
Article; Shao, Yan-Dong; Song, Huang-Wang; Feng, Wen; Wang, Xiang-Hui; Shi, Zai-Feng; Wu, Lu-Yong; Chen, Guang-Ying; Lin, Qiang; Letters in Organic Chemistry; vol. 15; 3; (2018); p. 206 – 213;,
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., Computed Properties of C12H12BrNO2

a) A solution of imidazole (13.6 g) in dry DMF (50 ml) was added dropwise to a stirred suspension of sodium hydride (8.0 g, 60% dispersion in oil) in dry DMF (250 ml) at ambient temperature under nitrogen for 2.5 hours. A slurry of N-(4-bromobutyl)phthalimide (53.6 g) in dry DMF (80 ml) was added and the mixture heated at 95 C. for 16 hours. The solvent was evaporated off under vacuum and the residue was extracted with hot toluene. The combined toluene extracts were evaporated to dryness and the residue triturated with ether and dried to give N-[4-(imidazol-1-yl)butyl]phthalimide, m.p. 76-79 C.

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; The Boots Company PLC; US5547972; (1996); A;,
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., Product Details of 5394-18-3

To a cooled solution of 1 /-/-imidazole (200 mg, 3.085 mmol, 1.05 eq) in DMF (7 ml_), NaH 60% in mineral oil (136 mg, 3.393 mmol, 1.1 eq.) was added portionwise and the mixture was stirred for 10 min. Afterwards, a solution of 2-(4-bromobutyl)-2,3-dihydro-1 7Aisoindole-1,3-dione (870 mg, 3.085 mmol, 1 eq.) in DMF (3 ml.) was added dropwise. The reaction was continued at 60C for further 16 h. The reaction was quenched with water and diluted in AcOEt. The layers were separated. Organic layer was dried, filtered off and concentrated in vacuo. The residue was purified by FCC (SiHP, DCM: MeOH 95:5) to afford the title compound (323 mg, 1.2 mmol, yield 40%) as a white solid. ESI-MS: 270 [M+H]+ 1H NMR (300 MHz, Chloroform-o) d 7.89 – 7.85 (m, 2H), 7.77 – 7.73 (m, 2H), 7.50 (t, J= 1.1Hz, 1H), 7.07 (t, J= 1.1Hz, 1H), 6.93 (t, J= 1.3 Hz, 1H), 4.02 (t, J= 7.0 Hz, 2H), 3.74 (t, J= 6.8 Hz, 2H), 1.91 – 1.79 (m, 2H), 1.78 – 1.64 (m, 2H).

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; RYVU THERAPEUTICS S.A.; DOBRZANSKA, Monika Patrycja; ZAWADZKA, Magdalena Izabela; RADZIMIERSKI, Adam; TOPOLNICKI, Grzegorz Witold; CWIERTNIA, Grzegorz Wojciech; MAHAJAN, Tushar Ravindra; FABRITIUS, Charles-Henry; CHMIELEWSKI, Stefan; GLUZA, Karolina Maria; ALVAREZ, Jose; ROGACKI, Maciej Krzysztof; MROCZKOWSKA, Magdalena; (215 pag.)WO2019/238786; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Formula: C12H12BrNO2

Cs2C03 (2 eq) was added to a solution of an alkyl bromide of general formula (IX) (1 eq) and amine of general formula (VIII) (1.1 eq.) in dry DMF with stirring. The mixture was stirred at 70C overnight or until consumption of the alkyl bromide. The reaction mixture was concentrated, extracted with EtOAc/H20. The organic phase was washed with brine, dried (MgS04), concentrated and purified by chromatography (mixtures of petroleum ether and EtOAc) to afford the bis-protected intermediate. General procedure 3 (alkylation). Starting materials: compound 2 and tert-butyl piperazine- 1-carboxylate.^-NMR (CDCI3) : delta 7.84 (m, 2H), 7.71 (m, 2H), 3.71 (t, 2H), 3.41 (t, 4H), 2.37 (m, 6H), 1.71 (m, 2H), 1.53 (m, 2H), 1.45 (s, 9H).

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.

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, category: indolines-derivatives

To the reaction flask was added 0.1 part of sodium hydride, 0.1 part of imidazole, 20 parts of tetrahydrofuranwere mixed evenly. Then, 0.08 parts of compound 1 was slowly added in dropwise manner, reacted at a temperatureat 50 for 1 h, filtered and air dried to collect compound 2, yield 85.5 %.

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.

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., Quality Control of 2-(4-Bromobutyl)isoindoline-1,3-dione

A 1.0 g portion of JV-[4- (bromo)butyl]phthalimide 21 (0.0035 mol) was dissolved in 10 mL of DMF, and to this solution was added 0.290 g (0.0044 mol) of sodium azide. The reaction was then allowed to stir for 5 h under nitrogen, after which the reaction mixture was concentrated in vacuo to yield a white semisolid. The semisolid was dissolved in water and extracted with three 50 mL portions of ethyl acetate, the combined organic layers were dried over anhydrous magnesium sulfate and filtered, and the solvent was removed to afford 22 (0.760 g, 88%) as a white amorphous powder. This preparation was used in the next reaction without further purification. 1H NMR (400 MHz CDCl3) delta 1.6-1.68 (m, 2H), 1.74-1.82 (m, 2H), 3.3 (t, J= 7.2 Hz, 2H), 3.7 (t, J= 7.2 Hz5 2H), 7.71-7.73 (m, 2H), 7.83-7.86 (m, 2H). 13C NMR(400 MHz CDCl3) delta 26.1, 28.6, 44.02, 53.6, 127.4, 128.0, 132.34, 134.12, 168.52, 171.0.

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.

Electric Literature 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.

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL × 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

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.

Electric Literature 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.

2-[4-(4-Morpholinyl)butyl]-1H-isoindole-1,3(2W)-dione (307). A mixture of 4- bromobutylphthalimide (10.0 g, 35.4 mmol), K2CO3 (5.88 g, 42.5 mmol) and morpholine (4.6 mL, 53.1 mmol) in DMF (100 mL) was stirred at 100 0C for 8 h, cooled to 20 0C and the solvent evaporated. The residue was partitioned between EtOAc (300 mL) and water (300 mL), the organic fraction washed with water (2 x 50 mL) and brine (50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with EtOAc, to give phthalimide 307 (9.59 g, 94%) as a clear oil: 1H NMR delta 7.81-7.86 (m, 2 H, Harom), EPO 7.68-7.73 (m, 2 H1 Haram), 3.66-3.72 (m, 6 H, 2 x CH2O, CH2N), 2.41 (br t, J = 4.5 Hz, 4 H, 2 x CH2N), 2.35 (br dd, J = 7.6, 7.4 Hz, 2 H, CH2N), 1.69-1.76 (m, 2 H, CH2), 1.50-1.58 (m, 2 H, CH2).

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:
Patent; AUCKLAND UNISERVICES LIMITED; WO2006/104406; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem