Category: indolines-derivatives

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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 4,7-Dichloroindoline-2,3-dione

General procedure: To a mixture of isatin 1a (14.7 mg, 0.1 mmol), H2O (5.4 muL, 0.3 mmol), quinine-derived amine 3 (3.3 mg, 0.01 mmol), and benzoic acid (3.66 mg, 0.03 mmol) in THF (1.0 mL) at 5 C was added acetaldehyde (22.0 mg, 0.5 mmol). After the reaction mixture was stirred for 15 h at this temperature, it was cooled to 0 C. Methanol (2 mL) and NaBH4 (20.0 mg, 0.5 mmol) were then added sequentially. The resulting reaction mixture was stirred for an additional 30 min at 0 C. Water (5.0 mL) was added to quench the reaction. The reaction mixture was extracted with ethyl acetate (10 mL x 3). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2 to 2:1) to give the pure product 2a.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Qunsheng; Zhao, John Cong-Gui; Tetrahedron Letters; vol. 53; 14; (2012); p. 1768 – 1771;,
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Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: N-(3-{1-[2-(1,3-Dioxoisoindolin-2-yl)ethyl]piperidin-4-yl}phenyl)acetamide (7a) N-[3-(Piperidin-4-yl) phenyl]-acetamide (6, 600 mg, 2.36 mmol), N-(2-bromoethyl)-phthalimide (720 mg, 2.83 mmol), and sodium carbonate(979 mg, 7.08 mmol) were dissolved in DMF (10 mL). After being stirred at 70C for 18 h, the mixture was diluted with water (50 mL), and extracted with ethyl acetate (50 mL×2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo, giving a residue that was subjected to column chromatography on silica gel (10% MeOH-CH2Cl2) to afford the title compound.

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-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lim, Chae Jo; Choi, Jun Young; Lee, Byung Ho; Oh, Kwang-Seok; Yi, Kyu Yang; Chemical and Pharmaceutical Bulletin; vol. 61; 12; (2013); p. 1239 – 1247;,
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Synthetic Route of 150544-04-0, 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. 150544-04-0, name is 6-Aminoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-dichloro-5-trifluoromethylpyrimidine (3.51 g; 16.2 mmol) in THF (100 mL) was added a solution of ZnCl2 (1M in ether; 16.2 mL). After 15 minutes 6-aminooxindole (2 g; 13.5 mmol) was added in small portions, followed by the dropwise addition of Et3N (1.63 g; 16.2 mmol) in 10 mL of THF. The reaction was then stirred at RT overnight. Following removal of the solvent under reduced pressure, the crude reaction was triturated from methanol and the product filtered off as a yellow solid 2.2 g (50percent yield). 1H NMR (DMSO-d6, 400 MHz) delta 3.40 (s, 2H), 7.13 (d, J=8.3 Hz, 2H), 7.20 (d, J=7.9 Hz; 1H), 7.27 (br s, 1H), 8.75 (s, 1H), 10.41 (s, 1H), 10.62 (s, 1H); HPLC ret. time: 5.933 min. LRMS (M+) 329.1, 331.0.

The chemical industry reduces the impact on the environment during synthesis 6-Aminoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US2005/256125; (2005); A1;,
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Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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. Application In Synthesis of 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(p-tolyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(methylphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5i): Melting point 222-224 C; white solid, 95%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.5 Hz, 1H), 4.66-4.70 (m, 1H), 4.30 (d, J = 10.0 Hz, 1H), 3.77 (d, J = 14.00 Hz, 1H), 3.67 (d, J = 15.00 Hz, 1H), 3.41-3.50 (dd, J = 15 Hz, 1H), 3.00-3.04 (dd, J = 14.5 Hz,1H), 2.70-2.75 (m, 1H), 2.55 (d, J = 14.0 Hz, 1H), 2.35 (s, 3H), 2.32 (s, 3H), 6.52 (d, J = 14.5 Hz, 1H), 6.58-7.48 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 21.1, 21.4, 39.5, 47.4, 52.8, 52.9, 61.1,66.9, 70.8, 100.7, 109.6, 119.5, 120.9, 121.5, 122.3, 123.9, 124.3, 126.3, 128.4, 128.5, 129.2, 129.4, 129.38, 130.5, 131.6, 133.7, 136.9, 138.3, 138.4, 138.7, 139.6, 139.8. 140.0, 144.3, 179.8, 197.1. EI-MS: m/z 739 (M+). Anal. Calcd for C46H40F3N3O3: C, 74.68; H, 5.45; N, 5.68. Found: C, 74.76; H, 5.53; N, 5.79.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 169037-23-4, its application will become more common.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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Related Products of 3339-73-9, 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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: An aqueous solution of metal (Li/Na) carbonate (4.5mmol in 50ml) was added drop wise to a well-stirred solution of NPA (9.1mmol) in ethanol (40ml) at room temperature separately. The pH (6-7) adjusted solution was stirred with heating (60C) for next 4h and then set aside for crystallization. After four weeks, 0.48g (48% yield) for each 1b and 2b of colourless single crystals were 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, 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nadeem, Muhammad; Bhatti, Moazzam H.; Yunus, Uzma; Mehmood, Mazhar; Asif, Hafiz Muhammad; Mehboob, Shoaib; Floerke, Ulrich; Inorganica Chimica Acta; vol. 479; (2018); p. 179 – 188;,
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Related Products of 883-44-3, 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 883-44-3 as follows.

INTERMEDIATE 3; 3-(fert-Butyldimethylsilanyloxy)propylamine; To a solution of N-(3-hydroxypropyl)phthalimide (5.25 g, 24.36 mmol) in DMF (20 niL) was added imidazole (16.6 g, 240 mmol) and tert-butyldimethylsilyl chloride (19 g, 120 mmol). The reaction was stirred at room temperature for 18 hours before the volatiles were removed in vacuo and a portion of the crude product was subjected to column chromatography (SiO2, 1:1 DCM/hexanes) to give 2-[3-(tert-butyldimethyl- silanyloxy)propyl]isoindole-l,3-dione as a clear oil (5 g). 2-[3-(tert-Butyldimetliyl- silanyloxy)propyl]isoindole-l,3-dione (5 g, 26.4 mmol) was dissolved in ethanol (50 ml) and methyl hydrazine (2.94 ml, 55.4 mmol) added. The reaction was heated to 75C for 8 hours before concentration in vacuo. The crude residue was triturated with a mixture of diethyl ether (150 mL) and hexanes (50 niL) and the resultant solid removed by filtration. The solvents were removed in vacuo to give the title compound as a pale yellow oil (1.8 g, 61%). deltaH (DMSOd6) 4.58 (2H, br s), 3.63-3.58 (2H, m), 2.67-2.62 (2H, m), 1.60-1.55 (2H, m), 0.83 (9H, d, J 1.1 Hz), 0.00 (6H, d, J 1.2 Hz). LCMS (ES+) RT 1.77 minutes, 190 (M+H)+.

According to the analysis of related databases, 883-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2007/88345; (2007); A1;,
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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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 356068-93-4

To a stirred solution of 1 (0.5 g, 1.67 mmol) in DMF( 35 mL) at room temperature was added HOBt(1.02 g, 7.52 mmol), triethylamine (2.12 mL, 15.03 mmol), ECDI HCl(1.44 g, 1.52 mmol) and methyl 3-aminopropanate hydrochloride(0.7 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the pH of solution was adjusted to 11-12 with 10 mol/L NaOH. The mixture was filtrated and the solid was collected washed with water, dried to obtain crude yellow solid product 110-2 (0.44 g, 68.3%). LCMS: m/z 386(M+1), 1H NMR(DMSO-J6) delta2.38 (s, 3H), 2.41 (s, 3H), 2.50 (t, 2H),3.44 ( t, 2H), 3.62 (s,3H), 6.85 (m, 2H), 7.71 (m,3H), 10.86 (s, IH), 13.69 (s, IH).

The synthetic route of 356068-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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Reference of 3485-84-5, 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. 3485-84-5 name is N-Vinylphthalimide, 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.

b) Racemic-cis-2-(2-phenyl-cyclopropyl)-isoindole-1,3-dione 2.00 g (7.29 mmol) benzaldehyde tosyl hydrazone are placed in 40 ml of tetrahydrofuran and cooled to -70 C. 7.29 ml (7.29 mmol) LiHMDS lithium bis(trimethylsilyl)amide (1 M solution in tetrahydrofuran) are added, then the mixture is stirred for 0.25 hours at -78 C. The reaction mixture is slowly heated to ambient temperature, then concentrated by evaporation. The residue is dissolved in 50 ml dioxane, combined with 0.166 g (1 mmol) benzyltriethylammonium chloride and 0.032 g rhodium acetate-dimer, and 6.31 g (36.45 mmol) 2-vinyl-isoindole-1,3-dione added. The reaction mixture is stirred for 80 hours, then extracted with water and dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography. Yield: 0.650 g (34% of theoretical)

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/116370; (2006); A1;,
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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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 675109-45-2

To a solution of 6-amino-2,3-dihydroisoindol-1-one (1.78 g, 12 mmol) in DMF/H2O (2:1, 75 ml) was added K2CO3 (3.32 g, 24 mmol, 2 eq.) and di-tert-butyl dicarbonate (5.67 g, 26 mmol, 2.2 eq.). The reaction was stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and water, and the organic layer was washed with saturated NaCl (aq), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and the resulting solid was filtered off to afford title compound (2.04 g, 68%). 1H NMR (360 MHz, d6 DMSO) ? 8.48 (1H, s), 7.83 (1H, d, J=1.2 Hz), 7.6 (1H, dd, J=8.2, 1.9 Hz), 7.43 (1H, d, J=8.2 Hz), 4.28 (2H, s), 1.49 (9H, s).

According to the analysis of related databases, 675109-45-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5181-35-1, name is 2-(2-Bromoethoxy)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 5181-35-1, Formula: C10H8BrNO3

(2) to 120mmol of compound III in 10mL of glacial acetic acid solution was added 15mL of 48% by weight of hydrobromic acid, stirred at 130 C for 5 minutes, cooled, filtered, the filtrate was concentrated to give a yellow compound IV

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:
Patent; Nanjing Tech University; Hu Xuhong; Li Song; (13 pag.)CN109678810; (2019); A;,
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