Author: Jessica.F

Reference of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

Intermediate 60 : 2-(3-(3-Oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (0587) A mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (499.4 mg, 2.458 mmol, commercially available from Fluorochem), piperazin-2-one (376.1 mg, 3.76 mmol, commercially available from Sigma Aldrich) and Na(0Ac)3BH (779.9 mg, 3.68 mmol) in 2-MeTHF (20 mL) was stirred at rt for 21 h 40 min. Further Na(OAc)3BH (516.6 mg, 2.437 mmol) was added after 3 h. AcOH (0.014 mL, 0.246 mmol) was added after 4 h 45 min. After 20 h 40 min further 2-MeTHF (5 mL) was added and the reaction mixture was heated to 60 C. Further Na(OAc)3BH (279.9 mg, 1.321 mmol) was added after 3 h 20 min at 60 C. Further Na(OAc)3BH (496.8 mg, 2.344 mmol) was added after 25 h 45 min at 60 C. The mixture was removed from heating and stirring after a total of 31 h at 60 C and cooled to rt. To this mixture was added sat. NaHCCte (2 mL) and water (8 mL). The mixture was stirred at rt for 20 min and extracted with EtOAc (3 x 10 mL). The organic layer was filtered through a cartridge fitted with a hydrophobic frit and the volatiles evaporated in vacuoto give an oil which was redissolved in MeOH (approx. 5 mL) and applied to the top of a 20 g Isolute aminopropyl ion exchange column. The column was eluted with 4 column volumes of MeOH and 4 column volumes of aqueous 2M HCI. The second MeOH fraction was evaporated in vacuoto give a pale yellow solid; 2-(3-(3-oxopiperazin- l-yl)propyl)isoindoline-l,3-dione (595.1 mg, 2.071 mmol, 84 % yield). (0588) LCMS (2 min high pH); Rt = 0.71 min, m/z = 288 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;,
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 14192-26-8 as follows. category: indolines-derivatives

Intermediate Ia (4Og) is dissolved in methanol (40OmL) and IM NaOH solution (420 mL) is added. The mixture is heated under reflux for 3 hours. The reaction is then neutralized with IM HCl. The methanol is then removed under reduced pressure and water is added EPO until precipitation commenced. The precipitate is collected via filtration, washed with water and dried under reduced pressure to yield the desired intermediate 2a (37g)

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 16800-68-3, A common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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.

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1504-06-9, name is 3-Methyloxindole, A new synthetic method of this compound is introduced below., Product Details of 1504-06-9

5-bromo-3-methyl-indol-2-one Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3) was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted with EtOAc (*3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120 C.; 1H NMR (DMSO) delta1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm-1; MS (EI) m/z 224/226 (M-H)-; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6780-38-7, 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 6780-38-7 as follows.

Take phthalylglycyl chloride (6.46g, 28.9mmol) a solution in dichloromethane (80 mL), add beta-phenylethylamine (3.55 mL, 28.2 mmol) and triethylamine (7.61 mL, 56.4 mmol). After stirring at room temperature for 1.5 h, add water (30 mL) and extract with dichloromethane (2¡Á40 mL). The organic layer was dried over magnesium sulfate and evaporated. The crude product was purified by crystallization from methanol (50 mL). Yielding a white solid indoleamine (8.20 g, 94%).

According to the analysis of related databases, 6780-38-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATIONAL HEALTH RESEARCH INSTITUTES; UENG,, SHAU HUA; YEH,, SHIU HWA; CHAO,, PO KUAN; SHIH,, CHUAN; (117 pag.)TW2019/12628; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 496-15-1, 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. 496-15-1, name is Indoline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of indoline (12) (1.19 g, 10.0 mmol) in sulfuric acid stirred at 0oCwas added KNO3 (1.2 g, 12.0 mmol) in several portions over 15 mins and the reactionmixture was stirred for 1 hr at this temperature and then heated to room temperature foranother 1 hr. After the reaction completed, the mixture was poured into ice-water, andextracted with AcOEt. The organic phase was washed with water and saturatedNaHCO3, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to give the 6-nitroindoline intermediate (13) 0.8 g, yield: 48.8%. 1H NMR (400 MHz, DMSO-d6) delta 7.38 (d, J = 7.9 Hz, 1H), 7.20 (d, J = 7.9 Hz, 1H), 7.15 (s, 1H), 6.15 (s, 1H), 3.53 (t, J = 8.6 Hz, 2H), 3.01 (t, J = 8.6 Hz, 2H). MS (ESI) m/z: 165 [M+H]+.

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

Reference:
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3, These common heterocyclic compound, 59-48-3, name is Indolin-2-one, 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.

Preparation of 5-Bromo-2-indolinone 2-indolinone (1.3 g) in 20 mL of acetonitrile was collected to -10 C. and 2.0 g of N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at 10 C. and 2 hours at 0. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of the title compound.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6316635; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

B. To a solution of 5-aminoindolin-2-one (8.76, 58.79 mmol) in tetrahydrofuran:dimethylformamide (400 mL:60 mL) was added trimethylsilylisocyanate (10.6 mL, 78.68 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 18 hours. A tan-colored solid formed which was isolated by filtration, washed with ether and dried in vacuo to afford 5-ureidoindolin-2-one (8.5 g).

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

Reference:
Patent; Schering Aktiengesellschaft; US2005/90541; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 446292-08-6, 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 446292-08-6 as follows.

Add 28 kg of rivaroxaban intermediate IV to 280 L of absolute ethanol, and add 36.5 kg of 40% methylamine solution.After refluxing for 1 h, the temperature was lowered to 50-60 C.Add 6N hydrochloric acid to adjust the pH to 2~3,Cool down to room temperature, centrifuge,Drying the filter cake to obtain rivaroxaban intermediate V(4-[4-[(5S)-5-(Aminomethyl)-2-oxo-3-oxazolidinyl]phenyl]-3-morpholinone hydrochloride) 19.66kg,The yield is 90.3%,The purity is 99.78%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qilu Pharmaceutical Co., Ltd.; Fan Chuanwen; Leng Chuanxin; Wang Yubing; Liu Peiyuan; (6 pag.)CN109553611; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C9H9NO

HNO3 (70% aqueous, 1.41 g, 22.4 mmol, 1.7 equiv) was slowly added to a solution of 1-methylindolin-2-one (2.00 g, 13.6 mmol, 1 equiv) in concentrated H2SO4 (8 mL) at 0C with stirring. After being stirred for 30 min, the mixture was poured onto a water/ice mixture (200mL). The resulting precipitate was collected by filtration and washed with water (250 mL) to give pure 1-methyl-5-nitroindolin-2-one (2.3g, 88%) as a tan solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem