Category: indolines-derivatives

Synthetic Route of 675109-45-2,Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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.

3H:; [00255] Intermediate 2 (164 mg, 1.11 mmol), 3G (535 mg, 1.00 mmol), and glyoxylic acid monohydrate (111 mg, 1.21 mmol) were taken up in CH3CN (3 mL) and DMF (2 ml). The mixture was stirred at 600C for 48 h, then was concentrated. The crude product was purified by flash chromatography (1 to 20% MeOH/CH2Cl2 gradient) to afford 313 mg of 3H as a pale yellow solid. MS (ESI) m/z 693.3 (M+H)+

The synthetic route of 675109-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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Electric Literature of 7699-18-5, 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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-methoxy-2,3-dihydro-1H-indole-2-one (5 g, 30.64 mmol) and diisopropylamine (6.14 g, 60.79 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added n-butyllithium (49 mL, 122.68 mmol, 2.5 M n-hexane solution).The mixture was stirred for 1 hour and 1,2-dibromoethane (6.89 g, 36.68 mmol) was slowly added.The mixed solution was transferred to room temperature for reaction. The reaction was then quenched by adding 100 mL of water,And extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over anhydrous sodium sulfate,Suction filtered and concentrated in vacuo. Passing a gradient flash column (ethyl acetate / petroleum ether) gave compound 10 as an off-white solid, 2.5 g, yield 43%.

The chemical industry reduces the impact on the environment during synthesis 5-Methoxyindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangdong Pharmaceutical University; Ye Lianbao; Shi Peiqi; Zhu Daqian; Zhao Tao; Chen Weiqiang; Gao Wei; Luo Yan; (27 pag.)CN110256429; (2019); A;,
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Reference of 774-47-0, 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 774-47-0 as follows.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

According to the analysis of related databases, 774-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

General procedure: A mixture of isatin (1 mmol), malononitrile or cyanoacetic esters (1 mmol), 1,3-dicarbonyl compounds (1 mmol), and the catalyst (10 wt %) in ethanol (3 ml) was stirred at 80 C for a specified time (see Table 2). After complete conversion, as indicated by TLC, the reaction mixture was cooled to room temperature. The resulting solid precipitate was filtered and dried along with the catalyst. Further purification of the product was performed by recrystallization using ethanol and the catalyst was recovered by filtration.

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 611-09-6.

Reference:
Article; Maheshwar Rao; Reddy, G. Niranjan; Reddy, T. Vijaikumar; Devi, B.L.A. Prabhavathi; Prasad; Yadav; Reddy, B.V. Subba; Tetrahedron Letters; vol. 54; 20; (2013); p. 2466 – 2471;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(2-Hydroxyethyl)isoindoline-1,3-dione

In the first step, under a nitrogen atmosphere, 3.00 mmol of thiacup [4] arene, 25.71 mmol of hydroxyethylphthalimide,9.15 mmol of triphenylphosphine, 120 mL of dry tetrahydrofuran (drying treatment before use), stir well and cool to zero in an ice-salt bath.9.14 mmol of diethyl azodicarboxylate was dissolved in 30 mL of dry tetrahydrofuran, and then placed in a constant pressure funnel and slowly dropped into a three-necked flask. After the dropwise addition was completed, the temperature was raised to room temperature for 72 hours.At the end of the reaction, the solvent was evaporated to dryness, and methanol was added while hot to precipitate a large amount of white solid. After suction filtration, the filter cake was dried.Purification by silica gel column chromatography (n-hexane: ethyl acetate = 8: 2) to obtain 2.43 g of 1,3-alternate-bis (2-phthalimide) thiacalix [4] arene, yield Is 75.8%,1,3-Alternate-bis (2-phthalimide) thiacalix [4] arene has the structural formula shown in Formula (II):

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenzhen Advanced Technology Institute; Zhao Jianglin; Jin Zongwen; Ruan Qin; Chen Zhenmin; Luo Qingying; Wu Yutian; (22 pag.)CN107936953; (2019); B;,
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Application of 1055412-47-9, 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. 1055412-47-9, name is su-5614 belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (120 mg, 0.44 mmol), morpholine (39 muL, 0.44 mmol) and paraformaldehyde (20 mg, 0.66 mmol) in 8 mL of dioxane and 2 mL of EtOH was heated to 80 C. for 15 h. The reaction mixture was cooled to room temperature and treated with morpholine (25 muL, 0.28 mmol) and paraformaldehyde (16 mg, 0.50 mmol) The reaction mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to room temperature and partially concentrated under a nitrogen stream. The reaction mixture was cooled to -20 C. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (85 mg, 52%) as an orange solid.

The synthetic route of su-5614 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2004/102509; (2004); A1;,
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Electric Literature of 60434-13-1, 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of N-benzylisatin (1a, 1.0 mmol), in dryTHF, trimethyl(trifluoromethyl)silane (TMSCF3,2.0 mmol) was added dropwise at room temperature. Tothis 0.052 g TBAF (20 mol %) was added and then thereaction mixture was stirred at room temperature untilcomplete conversion takes place as indicated by TLCanalysis. The reaction mixture was treated with aqueousNaHCO3 and was extracted with ethyl acetate. The organiclayers were collected and dried with anhydrous Na2SO4,followed by solvent removal under reduced pressure. Thecrude product was purified by flash chromatography(hexane/ethyl acetate = 90:10) on silica gel to give thedesired product.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bikshapathi, Raktani; Prathima, Parvathaneni Sai; Yashwanth; Pamanji; Jagadeeshkumar; Maheshwari; Rao, J. Venkateswara; Murty; Rao, V. Jayathirtha; Monatshefte fur Chemie; vol. 148; 4; (2017); p. 757 – 764;,
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Electric Literature of 39755-95-8, A common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, molecular formula is C9H7NO3, 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.

The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-Methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflux for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 1.1 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrazinocarbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. Product Details of 6941-75-9

Preparation of 5-bromo-2,3-dihydro-1H-isoindole (13); 564.2 ml of a 1M borane/THF solution are added dropwise to 42.5 g (188 mmol) of 5-bromoisoindole-1,3-dione in 300 ml of THF (dry) at -5 C. over a period of 60 min. The mixture is subsequently stirred for 2 h at 22 C. and then for 16 h at 80 C. The mixture is then cooled to 0 C., before 200 ml of methanol (exothermic.) and 200 ml of 2M hydrochloric acid are slowly added. The resultant mixture is stirred for 3 h at 80 C., cooled to 22 C., and 100 ml of water are added. The aqueous solution is extracted three times with 150 ml of dichloromethane each time, dried over sodium sulfate, filtered and evaporated to dryness: 5-bromo-2,3-dihydro-1H-isoindole; yield 15.4 g of ?13? (41.3%); MW 198.06; Rt 1.099 min (?polar? method).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent Gesellschaft Mit Beschrankter Haftung; US2010/311745; (2010); A1;,
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Electric Literature of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 90a: 5-Bromoindolin-2-one (Compound 0601-194)To a mixture of 5-bromoindole-2,3-dione (2.25 g, 10 mmol), ethyleneglycol (45 mL) and hydrazine hydrate (1.06 g, 21.10 mmol) was added KOH (1.68 g, 30 mmol). The reaction mixture was stirred at 80C for 4 hours. The mixture was cooled to room temperature and poured into ice cold water and the mixture was adjusted to pH 1-2 with 12N hydrochloric acid and stirred at room temperature for 12 hours. The mixture was filtered and solid was washed with water (5 mL) and dried to get the crude product which was purified by column chromatography on silica gel (methanol in dichloromethane, 0.5% v/v) to give 0601-194 (785 mg, 37%) as a yellow solid. LCMS: 214 [M+l]+. 1H-NMR (400 MHz. OMSO-de) delta 3.51 (s, 2H), 6.76 (d, J= 8.0 Hz, 1H), 7.34 (dd, J= 8.0, 2.0 Hz, 1H), 7.38 (m, 1H), 10.49 (s, 1H).

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, 5-Bromoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng; WO2011/130628; (2011); A1;,
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