Author: tianli

2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 62 : 2-f3-f4-Methyl-3-oxopiperazin-l-vnpropynisoindoline-l,3- dione (0595) To a mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (515 mg, 2.53 mmol, commercially available from Fluorochem) and Na(OAc)3BH (815.9 mg, 3.85 mmol) in 2-MeTHF (20 mL) was added l-methylpiperazin-2-one (0.420 mL, 3.82 mmol, commercially available from Fluorochem). The mixture was stirred at rt for 4 h 45 min. To the reaction mixture was added aqueous 2M Na2C03 (10 mL) and this mixture stirred at rt for 10 min giving an aqueous phase at approximately pH 10. The layers were separated and the aqueous layer washed with EtOAc (2 x 10 mL). The organic layers were filtered through a cartridge fitted with a hydrophobic frit and the filtrate evaporated in vacuo to give a pale yellow crystalline solid. 2-(3-(4-methyl-3-oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (660.5 mg, 2.192 mmol, 86 % yield). (0596) LCMS (2 min high pH); Rt = 0.74 min, m/z = 302 for [MH]+

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); 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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 6326-79-0

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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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;,
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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. 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;,
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These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

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 15362-40-0.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
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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;,
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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

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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., 1168150-46-6

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

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; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
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20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

Under argon, 2.64 g (66 mmol) of sodium hydride (60% in mineral oil) were suspended in 25 ml of THF and cooled to 0 C. A solution of 4.00 g (18.86 mmol) of 5-bromo-1,3-dihydro-2H-indol-2-one in 25 ml of DMF was added dropwise and the mixture was stirred at 0 C. for 30 min. Subsequently, 4.11 ml (66 mmol) of methyl iodide were slowly added dropwise thereto, then the reaction mixture was warmed to RT and stirring continued at this temperature overnight. For workup, the mixture was poured onto 200 ml of 1M hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed with water, then a saturated sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue was dissolved in 200 ml of acetonitrile and the mineral oil was extracted with n-pentane. The acetonitrile phase removed was concentrated on a rotary evaporator and the remaining brownish solid was dried under HV. This gave 4.45 g (84% of theory) of the title compound in 91% purity. LC-MS (Method 3): Rt=1.18 min; m/z=254, 256 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.27 (s, 6H), 3.12 (s, 3H), 6.99 (d, 1H), 7.45 (dd, 1H), 7.60 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
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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;,
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