Month: June 2021

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. 193354-13-1, name is 5-Iodoindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6INO

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white 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:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. COA of Formula: C10H9NO2

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. Application In Synthesis of 7-Chloroisatin

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

The synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 102359-00-2, 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. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, 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.

1-[5-(Morpholine-4-carbonyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), morpholine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(morpholine-4-carbonyl)-1,3-dihydro-indol-2-one. 1NMR (300 MHz, DMSO-d6) delta 10.54 (br s, 1H, NH), 7.24 (m, 2H), 6.83 (d, J=7.6 Hz, 1H), 3.56 (m, 4H, 2*CH2), 3.49 (s, 2H, CH2), 3.47 (m, 4H, 2*CH2). MS APCI neg. m/z 245 [M+-1].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxoindoline-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H7NO2

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

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; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3891-07-4, 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.

Example 7 : 2-({2-[2-(4-{(2S)-2-Hydroxy-3-[(methylethyl)amino]propoxy}phenoxy) acetylamino] ETHOXY} METHYL)-4-(2-CHLOROPHENYL)-5-CYANO-6-METLLYL-1, 4- dihydropyridine-3-carboxylate is synthesized according to Scheme VI. SCHEME VI 0 Ho- p OEt HO out C1 Ni C1 Me NC Me N N CHO CHO ci NC Me H 0 1. acetone, II. — . HO /O 2. II wEthyl 4- [2-FL, 3-DIOXOISOMDOLM-2-YDETHOXY1-3-OXOBUTANOATE. A solution of 2- (2- hydroxyethyl) isoindoline-1, 3-dione (10 g; 52.31 mmol) in DMF (150 ml) is cooled to 0C and treated with 1. 1 equivalents of a 60% dispersion of sodium hydride in mineral oil. After gas evolution has ceased, ethyl 4-chloro-3-oxobutanoate (7.75 g; 47.08 mmol) in 20 ml of DMF is added drop-wise, and the resulting solution is stirred overnight at room temperature. The pH of the mixture is then adjusted to 6-7 by the addition of 1 N HC1, and the product is partitioned between H2O and EtOAc. The aqueous phase is extracted again with EtOAc, and the combined organic phases are washed with water and brine, dried over magnesium sulfate, and concentrated to a crude residue, which is purified on a silica gel column, eluting with 25% EtOAc in hexane to obtain 7.52 g (23.54 mmol ; 50%) of the product as an oil.

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

Reference:
Patent; ARTESIAN THERAPEUTICS, INC.; WO2005/16885; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 667463-64-1, 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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, 6-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Formula: C8H4ClNO2

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. COA of Formula: C8H4BrNO2

280 ml of 1M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at 0 C. then heated at reflux overnight. The reaction was cooled to 0 C. then treated cautiously with methanol (100 ml) followed by 2M HCl (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (×3). The aqueous was basified with 2M NaOH then extracted with DCM (×3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1H, d), 7.20 (1H, d), 4.05 (4H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem