Tag: M.W=100-200

Synthetic Route of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Example 99 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,4,6-trifluorobenzyl)urea Diphenylphosphoryl azide (198 mg, 0.72 mmol, 1.2 eq) and triethylamine (73 mg, 0.72 mmol, 1.2 eq) were added to a solution of 2,4,6-trifluorophenylacetic acid (114 mg, 0.60 mmol) in toluene, and the mixture wasstirred at 110C for 60 min. Thereafter, 4-aminophthalimide (97 mg, 0.60 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (97 mg, 46.4%). MS m/z: 349 1H-NMR delta: 4.36 (2H, d, J = 4.64 Hz), 6.91 (1H, t, J = 5.73 Hz), 7.19 (2H, t, J = 8.66 Hz), 7.57 (1H, dd, J = 1.71, 8.05 Hz), 7.66 (1H, d, J = 8.29 Hz), 7.98 (1H, d, J = 1.71 Hz), 9.17 (1H, s), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); 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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Nitrophthalimide

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
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Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4, category: indolines-derivatives

To a stirred solution of 1,6-dibromohexane (12.3 mL, 81.0 mmol) in DMF (10 mL), was added potassium phthalate (5.0 g, 27.0 mmol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90 C for 18 h, then quenched with water (300 mL) and extracted with diethyl ether (150 mL x 2). The combined organic extracts were washed with water (100 mL x 2), followed by brine (50 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 3-i as an off- white solid (6.3 g, 76% yield). LCMS: 310.95 (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, Potassium 1,3-dioxoisoindolin-2-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LEWIS, Michael; (300 pag.)WO2018/98204; (2018); A1;,
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Related Products of 19155-24-9, 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. 19155-24-9 name is 3,3-Dimethylindolin-2-one, 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 5-Chloroacetyl-3,3-dimethyl-2H-indol-2-one 10.8 g (66.4 mmoles) 3,3-dimethyl-3H-indol-2-one are slowly added (in 1 h) to a suspension of 26 7 g (200 mmoles) aluminium chloride and 15 g, that is 10.58 ml (133 mmoles) chloroacetyl chloride in 60 ml dichloromethane, then the mixture is heated under reflux for 1 h 30 min. The brown suspension obtained is slowly poured into 500 ml ice-water, the mixture is stirred for 30 min and then filtered and the solid is washed with a little ether and dried. 16.3 g of crystals are obtained, which are used as such in the following step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dimethylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Synthelabo; US5034401; (1991); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 25 mL oven-dried Schlenk tube was sequentially added N-methylaniline 1 or aniline 4 (0.2 mmol), Ethyl Bromodifluoroacetate 2a (81.2 mg, 0.4 mmol), DMF (1ml) and H2O (1 mL) was added under air. The reaction mixture was stirred for 6 h at 110. The solution was then diluted with ethyl acetate (20 mL), washed with brine (10 mL), extracted with ethyl acetate (3*5 mL), dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The crude reaction mixture was purified by column chromatography (silica gel, ethyl acetate/petroleum ether) yielded the desired product 3 or 5.

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-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Zhuo-Wei; Xu, Wen-Yi; Pei, Xiao-Jun; Tang, Fei; Feng, Yi-Si; Tetrahedron Letters; vol. 60; 18; (2019); p. 1254 – 1258;,
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Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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 silver sulfate (100 g, 0. 32 mol) and iodine (82 g, 0.32 mol) IN NN-DIMETHYLFORMAMIDE (700 mL) and ethanol (1400 mL) was treated with 5-nitro-2, 3-DIHYDRO-1H-INDOLE I (48 G, 0. 29 mol). The resulting mixture was stirred at 25C for 1.5 h, filtered and the filter pad washed with ethyl acetate. The filtrate was concentrated in vacuo to a volume of approximately 500 mL. This solution was treated with a L. oN aqueous sodium thiosulfate solution (100 mL) and a saturated aqueous sodium chloride solution (400 mL). The resulting precipitate was collected by filtration, washed with water and petroleum ether, and dried in vacuo to afford 7-IODO-5-NITRO-2, 3-DIHYDRO-1H-INDOLE II (83.9 G, 98. 9%) as a white solid: 1H NMR (DMSO-D6, 300 MHz) 8 8. 18 (d, J = 2. 20 Hz, 1H), 7. 80 (d, J = 1. 46 Hz, 1H), 7. 03 (broad s, 1H), 3.65 (t, J = 8. 97 Hz, 2H), 3. 17 (t, J = 8. 60 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/101568; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 a solution of potassium 1,3-dioxoisoindolin-2-ide (125.0 g, 678.1 mmol) in DMF (500 mL) was added 1-chloropropan-2-one (57 g, 594.0 mmol), the reaction mixture was stirred at ambient temperature for about 60 h. The reaction mixture was poured into ice water (1.0 L), the resulting mixture was stirred for about 1 h. The precipitate was collected by filtration and dried in vacuum to afford the product as a white solid (101.2 g, 8 1.3%). MS (ESI, m/e) [M+1] 203.9.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; WANG, Zhiwei; GUO, Yunhang; YU, Desheng; (98 pag.)WO2019/34009; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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: Potassiumhydroxide (0.35 g,6.17 mmol) was added to a solution of 4-aminophthalimide 10 (1.00 g, 6.17 mmol) in dimethylformamide(30 mL) and the mixture was stirred at ambient temperature for 2 h. Iodomethane (0.88 g, 6.17 mmol) wasadded and it was stirred for another 18 h at the same temperature. Water (50 mL) and ethyl acetate (50 mL)was added and the resulting phases were separated. The organic phase was washed with brine, driedover sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient:0-100% ethyl acetate in cyclohexane) afforded the title compound 11a as a yellow solid (1.00 g, 92% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Article; Fischer, Thomas; Riedl, Rainer; Molecules; vol. 22; 9; (2017);,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-one, 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 16800-68-3, COA of Formula: C10H9NO2

3 – (4 – Fluorophenyl) propyne acid 4 – nitrophenyl-unitz (85.5 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 31 mg and gave rise 65% to unit_.

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; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, molecular formula is C9H6FNO2, 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

20.64 mg of N-methyl-7-fluoroisidine, 27.22 mg (28.06 mL) of trimethyl orthoformate and an appropriate amount of phosphotungstic acid were charged in a IOOmL flask, and the mixture was stirred at room temperature with Thin layer chromatography to determine whether there is a new product generation and tracking the progress of the reaction, the reaction is complete, add appropriate amount of triethylamine neutralization reaction to neutral, the reaction is complete after the reaction solution evaporated under pressure, the concentrate water, solid matter Precipitation, filtration, washing filter cake, the target product to obtain crude products, recrystallization can be pure target products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 875003-43-3, its application will become more common.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Jia Minyi; Song Huihui; (15 pag.)CN106632365; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem