Tag: M.W=100-200

Electric Literature of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of Methyl 4-12-(PHTHALIMIDO) ETHOXY] ACETOACETATE (XV) A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 60 mL of tetrahydrofuran under nitrogen atmosphere. 3.14 g sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 10 g OF N-(2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 7.48 g ethyl 4-chloroacetoacetate in 25 mL of tetrahydrafuran was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 5 mL ethanol. The mixture was then poured into 100 mL of 1N hydrochloric acid solution in crushed ice and 150 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 50 mL of 5 wt. % OF NHC03 solution, then with 100 mL of water, dried over 5 G ofMgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 10 ML of hexane to remove the mineral oil to give 8.87 g of methyl 4-[2-(PHTHALIMIDO) ethoxy] aceto acetate as a light brown product (yield 55%, rel. compound purity > 95%). IR (KBR. CM~L . : 2995 and 1716.-1H-NMR (CDC13) 8 7.80 (dd, 2H), 7.70 (dd, 2H), 4.11 (s, 2H), 3.87 (t, 2H), 3.75 (T, 2H), 3.61 (s, 3H), 3.44 (s, 2H). 13C-NMR (CDC13) 6 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 52.8, 46.0, 37.4.

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-(2-Hydroxyethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
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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. 21857-45-4, name is 5-Methoxyindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Methoxyindoline

General procedure: The mixture of xylene (1.0 mL), substrate (0.3 mmol), and rGO (100 w%) was stirred at 100 C for 12 h under O2 atmosphere. After the reaction, the mixture was diluted with AcOEt and water. The organic phase was concentrated under reduced pressure, and purified by column chromatography with silica gel.

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 21857-45-4.

Reference:
Article; Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; 1; (2016); p. 21 – 23;,
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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 61-70-1 as follows. Application In Synthesis of 1-Methylindolin-2-one

To 10 ml schlenk bottle adding N – methyl -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N – methyl -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N – methyl isatin, I – 2, the isolation yield is 73%,1

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
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Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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 8 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (82 mg, 0.2 mmol), 2-oxoindoline-6-carboxylic acid (36 mg, 0.2 mmol), EDCI (76 mg, 0.4 mmol) and N-methylimidazole (50 mg, 0.6 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by preparative TLC (Silica gel, 20 cm*20 cm, separated by EtOAc, eluted by DCM_MeOH=1:20, v/v) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide (25 mg, 23.5%). 1H NMR (300 MHz, DMSO): delta 10.52 (s, 1H), 9.56 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 7.90 (brs, 1H), 7.48-7.46 (m, 2H), 7.28-7.25 (m, 2H), 6.93-6.90 (m, 1H), 4.54 (brs, 1H), 3.77-3.34 (m, 11H), 2.50-2.34 (m, 1H), 2.07-1.99 (m, 2H). LC-MS: 532 [M+H]+, 530 [M-H]-, tR=1.35 min. HPLC: 97.39% at 214 nm, 97.05% at 254 nm, tR=4.54 min.

Statistics shows that 2-Oxoindoline-6-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 334952-09-9.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Indoline – Wikipedia,
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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;,
Indoline – Wikipedia,
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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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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);,
Indoline – Wikipedia,
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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;,
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. 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
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