Tag: M.W=100-200

3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2518-24-3, 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. 2518-24-3 name is 4-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.

3-Aminophthalimide (2.00 g, 12.3 mmol) was dissolved in methanol (200 mL), and the solution was added with N-bromosuccinimide (2.19 g, 12.3 mmol), followed by stirring at room temperature for 50 minutes. The obtained solid was collected by filtration and washed with methanol to obtain 3-amino-6-bromophthalimide (2.21 g, yield 74%). APCI-MS m/z: 241 [M-H]-; 1H-NMR (DMSO-d6)delta(ppm): 6.53 (br s, 2H), 6.88 (d, J = 8.9 Hz, 1H), 7.49 (d, J = 8.9 Hz, 1H), 11.07 (br s, 1H).

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

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2108642; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8. 496-12-8

Example 66 Preparation of 2-(4-(2-(Isoindolin-2-yl)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one To a suspension of 2-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.50 g, 1.15 mmol) in anhydrous DMF (9 mL) was added isoindoline (0.41 mL, 3.46 mmol) and the reaction mixture was stirred at room temperature for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was triturated with water (50 mL). The separated solid was filtered, washed with water and ether, and dried under vacuum to give the title compound as a white solid. Yield: 0.45 g (83%). MP 202-202.5 C. 1H NMR (400 MHz, CDCl3): delta 10.09 (br s, 1H), 7.77 (s, 2H), 7.22 (br s, 4H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 4.11 (s, 4H), 4.03 (t, J=6.0 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.22 (t, J=6.0 Hz, 2H), 2.42 (s, 6H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of Isoindoline.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-one, molecular formula is C9H9NO, 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. 61-70-1.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

The synthetic route of 1-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, Name is 1-Methylisatin, 2058-74-4, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: A mixture of isatin derivative (1.0mmol), activated methylene (1.0mmol), 1,3-diketones (1.0mmol), and Fe3O4SiO2-imid-PMAn catalyst (0.8mol%) was stirred at 70C in water or irradiated in a microwave oven at 200W for an appropriate period of time as indicated in Table 2. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with hot ethanol (10mL). The catalyst was removed by using a magnetic field and then the solvent was evaporated and the pure product was obtained by recrystallization from ethanol.

Statistics shows that 1-Methylisatin is playing an increasingly important role. we look forward to future research findings about 2058-74-4.

Reference:
Article; Esmaeilpour, Mohsen; Javidi, Jaber; Divar, Masoumeh; Journal of Magnetism and Magnetic Materials; vol. 423; (2017); p. 232 – 240;,
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 39755-95-8 as follows. 39755-95-8

General procedure: The preparation was divided into two steps. Firstly, substituent indoline-2,3-dione (1 equiv) was dissolved in ethanol (10 mL), hydrazine hydrate (2 mL) was added. The reaction mixture was refluxed with magnetic stirring for 3 h and cooled to 0 C, then sodium hydroxide (3 equiv) was added, refluxed for 0.5 h and cooled to room temperature, then 150 mL water was added. The mixture was acidified by adding 2 N hydrochloric acid to pH 2, and extracted twice with dichloromethane. The organic filtrate was washed twice with brine, dried (Na2SO4), and then concentrated to give corresponding indolin-2-one by high-vacuum drying. Secondly, a mixture of the corresponding indolin-2-one (1 equiv) and furan-2-carbaldehyde (1 equiv) in ethanol was added two drops of piperidine and refluxed with magnetic stirring for 5 h. After the mixture cooled, the precipitate was filtered, washed with cold ethanol, dried, and recrystallized from methanol to afford the terminal product.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhong, Ye; Xue, Mengzhu; Zhao, Xue; Yuan, Jun; Liu, Xiaofeng; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Xu, Yufang; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1724 – 1734;,
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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., 774-47-0

EXAMPLE 4 5-fluoro-6-(4-methylpiperazinyl)isatin STR12 To a solution of 5,6-difluoroisatin (1.0 g, 5 mmol) in 50 mL of dimethyl sulfoxide was added N-methylpiperazine (5.47 g, 50 mmol). The mixture was stirred for 4 h at room temperature and the crude reaction mixture was diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate. The organic layers were separated and concentrated to give the title compound in 72% yield: mp 150 C. (dec); 1 H NMR (300 MHz, DMSO-d6)delta 10.8 (br s, 1H), 7.3 (d, 1H), 6.4 (d, 1H), 2.25 (s, 3H), 2.2 (m, 4H), 2.1 (m, 4H).

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; PathoGenesis Corporation; US5441955; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1127-59-9, Adding a certain compound to certain chemical reactions, such as: 1127-59-9, name is 7-Methylindoline-2,3-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 1127-59-9.

General procedure: A solution of isatin derivatives 1 (0.4 mmol), 3-methyl-4-nitro-5-alkenyl-isoxazoles 2 (0.6 mmol) and proline or thioproline or sarcosine (0.8 mmol) in 10.0 mL of CH3CN at 80 ¡ãC for 24 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc5:1-3:1) to furnish the corresponding products 3-5.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiong-Wei; Yao, Zhen; Yang, Jun; Chen, Zhi-Yong; Liu, Xiong-Li; Zhao, Zhi; Lu, Yi; Zhou, Ying; Cao, Yu; Tetrahedron; vol. 72; 10; (2016); p. 1364 – 1374;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2518-24-3, Adding some certain compound to certain chemical reactions, such as: 2518-24-3, name is 4-Aminoisoindoline-1,3-dione, 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 2518-24-3.

Step 2: 4-Iodo-l,3-isoindolinedione; A ~3.6M aqueous solution of sodium nitrite was added at 0C to a -2.0M solution of the product obtained from step 1 in concentrated hydrochloric acid. After stirring the mixture at the same temperature for 10 min., a ~3.39M aqueous solution of potassium iodide was added to it, allowed to warm up to RT and then heated at 800C for 2h. After cooling toRT, work-up (AcOEt/H2O) afforded the title compound in 82% yield. 1H-NMR (delta ppm,DMSO-J6, 300 MHz): 11.48 (br. s, IH); 8.17 (d, J = 7.8, IH); 7.79 (d, J = 8.4, IH); 7.48 (t, J = 6.9, IH).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2518-24-3.

Reference:
Patent; GLENMARK PHARMACEUTICALS, S. A.; WO2009/118596; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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. 3484-35-3.

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methyl-3-(propan-2-ylidene)indolin-2-one (7h): Prepared from 5-methyl-2-oxindole according to RP 1 on a 924 mmol scale. The title compound (110 mg, 587 mmol, 63 %) was obtained as an orange solid. RF 0.67 (P/EA1 : 1; UV). numax (ATR)/cm1 3167br (NH), 3148w, 3025m, 2913w, 2858w,1698vs (CO), 1614s, 1480vs, 1316m, 1249m, 1211m. deltaH(CDCl3, 250 MHz, 300 K) 8.12 (1H, br s, NH), 7.34 (1H, br s,H-4), 7.01 (1H, br d, 3J 7.8, H-6), 6.77 (1H, d, 3J 7.8, H-7), 2.61(3H, s, CH3), 2.39 (3H, s, H-30), 2.36 (s, 3H, H-10). deltaC (CDCl3,63 MHz, 300 K) 169.5 (s, C-2), 156.2 (s, C-3′), 136.7 (s, C-7a),131.0 (s, C-5), 128.0 (d, C-6), 124.5 (s, C-4), 124.4 (d, C-3),122.9 (s, C-3a), 109.1 (d, C-7), 25.4 (q,CH3), 23.3 (q, C-1′), 21.4(q, C-3′). m/z (HRMS ESI) 188.1070; [M H](C12H13NO)requires 188.1017.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem