Tag: M.W=100-200

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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., name: Indolin-2-one

The starting material was prepared as follows: Fuming nitric acid (1.58 ml, 39.4 mmol) was added dropwise to a solution of oxindole (5 g, 37.5 mmol) in concentrated sulphuric acid (25 ml) cooled by an ice bath and maintained below 5 C. The mixture was stirred for 30 minutes at 0 C. and then poured into water. The precipitate was collected by filtration and thoroughly washed with water. The solid was suspended in 50% acetic acid (100 ml) and heated at 90 C. for 1 hour. The mixture was allowed to cool, the solid product was collected by filtration, washed with water and dried under vacuum over phosphorus pentoxide at 40 C. to give 5-nitrooxindole (3.2 g, 48%). 1H NMR Spectrum: (CDCl3, CD3CO2D) 3.68(s, 2H); 7.05(d, 1H); 8.16(s, 1H); 8.22(s, 1H) MS-EI: 178 [M]+

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; Zeneca Limited; US6265411; (2001); B1;,
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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 317-20-4

To a stirred solution of 7-fluoroindoline-2,3-dione (500 mg, 3.03 mmol) in DMF (5 mL) were successively added K2C03 (502 mg, 3.63 mmol) and methyl iodide (0.199 mL, 3.18 mmol). The resulting mixture was stirred at RT for 1 hr. The mixture was quenched with water, diluted with EtOAc and saturated aqueous NaHC03 solution and both phases were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure to afford the title product (497 mg, 2.219 mmol, 73.3% yield) as yellow solid. Rt = 0.69 min (UPLC-MS); ESI-MS = 179.9 [M+1]+ (UPLC-MS).

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 317-20-4.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 3.25 g, 10.5 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 12(17), pp 2427-2430) (1.96 g, 10.0 mmol) in dry acetonitrile (12 mL) was added 3-picoline (2.60 g, 28 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (1.48 g, 12.9 mmol) was added dropwise at 0-10 C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 2 hours. Then additional quantities of 3-picoline (0.37 g, 4.0 mmol) and methanesulfonyl chloride (0.24 g, 2.1 mmol) were added, and stirring was continued at room temperature for 3 hours. The mixture was cooled to 0 C, water (6 mL) was added dropwise, and stirring at 0-5 0C was continued for 1 hour. Then the mixture was filtered, and the solids were washed with 2:1 acetonitrile-water (3 x 3 mL), and dried under nitrogen to afford the 3-picoline salt of the title compound as a light green solid, 1.23 g. EPO The isolated solid was suspended in acetonitrile (3 mL) and IN aqueous hydrochloric acid (3 mL) was added dropwise. The solids dissolved, and then a new precipitate formed. The mixture was stirred at room temperature for 1 hour, and the precipitate was filtered, washed with 1 : 1 acetonitrile-water (3 x 2 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as an off-white solid, 0.27 g (5.6% yield), m.p. 139-142 0C.1H NMR (DMSO-^6) delta 2.22 (s, 3H), 7.29 (s, IH), 7.58 (d, J = 2.4 Hz, IH), 7.61 (dd, J = 8.2, 4.6 Hz, IH), 7.71 (d, J = 2.4 Hz, IH), 8.17 (dd, / = 8.2, 1.4 Hz, IH), 8.49 (dd, J = 4.6, 1.4 Hz, IH), 10.57 (br s, IH).

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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 stirred solution of compound 11 (100 mg, 0.245 mmol) in DMF (4 mL) was added diisopropylethylamine (DiPEA) (95 mg, 0.735 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (112 mg, 0.294 mmol) followed by addition of aryl or aliphatic amines (12a-m) (0.279 mmol) and stirred at room temperature for 18 h. After completion reaction mixture was poured into ice cold water extracted with ethyl acetate (2 ¡Á 15 mL), combined extracts were washed with brine solution, dried over anhy. Na2SO4 and concentrated under reduced pressure to afford crude product. This crude compound was purified by column chromatography (elutent:2 % methaol: CH2Cl2) to affords pure compounds 13a-m as yields of the products varied between 80-94 %. By adapting this procedure the compounds 13a-13m were synthesized (Scheme-II).

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

Reference:
Article; Tharikoppula, Giri; Eppakayala, Laxminarayana; Maringanti, Thirumala Chary; Kamalapuram, Chiranjeevi; Kudle, Karunakar Rao; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1515 – 1521;,
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 341988-36-1 as follows. name: Methyl indoline-6-carboxylate

Dihydroindole-6-carboxylic acid methyl ester (3.60 g, 0.02 mol) was dissolved in a 100 mL single-mouth bottle containing 50 mL of ethanol:water (4:1), and 10 mL (2M aqueous potassium hydroxide solution) was added at 45 ¡ã C. The reaction was carried out for 2 hours. After the reaction was completed, the reaction mixture was neutralized with a 2M aqueous hydrochloric acid solution to pH=6, and then extracted with dichloromethane (150 mL¡Á3).The combined organic phases were dried and concentrated to give the title compound.

According to the analysis of related databases, 341988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Ge Chongxun; Huang Yiqiang; Cao Chen; Li Qingqing; Hou Shaohua; (63 pag.)CN108276382; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).?H NMR (400 MHz, CDC13): 7.82 (dd,J= 5.5, 3.1 Hz, 2H), 7.69 (dd,J= 5.5, 3.0 Hz, 2H), 3.68 (t, J 7.2 Hz, 2H), 3.38 (t, J 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H),1.53-1.43 (m, 2H).

Statistics shows that Potassium 1,3-dioxoisoindolin-2-ide is playing an increasingly important role. we look forward to future research findings about 1074-82-4.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (340 pag.)WO2018/98207; (2018); 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

Application of 150560-58-0, 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. 150560-58-0, name is 5-Isopropylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL¡Á4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

The synthetic route of 5-Isopropylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

110568-64-4, name is 6-Nitroisoindolin-1-one, 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. HPLC of Formula: C8H6N2O3

Intermediate 6[00204] A suspension of Intermediate 6B (1.6 g, 8.98 mmol) and Pd/C (0.18 g) in MeOH (100 mL) was stirred under H2 (1 atm) for 4 h. The reaction mixture was filtered and the filter cake was washed with MeOH. The combined filtrates were concentrated in vacuo. The crude solid was triturated with MeOH (10 mL) and dried in vacuo to yield Intermediate 6 (800 mg, 5.40 mmol, 60.1 % yield) as a beige solid. 1H NMR (400 MHz, DMSOd6) delta ppm 4.15 (s, 2 H) 5.26 (s, 2 H) 6.77 (dd, J=8.25,2.20 Hz, 1 H) 6.80 (s, 1 H) 7.16 (d, J=8.79 Hz, 1 H) 8.29 (s, 1 H). MS (ESI) m/z 149.2 (M+H)+.

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, 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. 19155-24-9 name is 3,3-Dimethylindolin-2-one, 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.

Example 1 5-amino-l-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et.al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of cone, sulfuric acid using mechanical stirring and cooled using a -40 C cooling bath until stirring became difficult. A solution of 10.1 ml of fuming nitric acid and 50 ml of cone, sulfuric acid was added dropwise and the reaction allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 3Ig).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dimethylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; WO2007/120339; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem