Author: Jessica.F

Electric Literature of 16800-68-3, 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.

General procedure: To 5-bromo-N-acetyl indoxyl (0.018 mole), Titanium isopropoxide (0.027 mole) was added under nitrogen atmosphere. The mass was stirred for 30 min at room temperature. N-Methyl piperazine (0.02 mole) was added neat to the above complex. The reaction mass was further at room temperature for 5 hr. Absolute ethanol (20 mL) was added to the thick slurry mass followed by the addition of sodium triacetoxyborohydride (0.036 mole). After completion of the reaction (TLC), the reaction mass was diluted with water (100 mL) and the precipitated titanium complex was removed by filtration. The solid on the filter was washed with ethyl acetate till colourless filtrate was obtained. The filtrate was basified with aqueous ammonia whereby compound went into organic layer. The organic layer was separated, washed with brine solution (1 x 50 mL) and dried over anhydrous magnesium sulfate. Solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using 70 % ethylacetate in n-hexane to obtain the title compound in 70% yield.

Statistics shows that 1-Acetylindolin-3-one is playing an increasingly important role. we look forward to future research findings about 16800-68-3.

Reference:
Article; Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 346 – 349;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 324-03-8, SDS of cas: 324-03-8

Weigh rapamycin (0.05mmol), isatin 3g (0.10mmol) and rhodium octanoate (0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary evaporation to give a crude product. The rapamycin analog I-g was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 88%.

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

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3335-98-6, 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. 3335-98-6 name is 1-Phenyloxindole, 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.

General procedure: The reaction mixture of the substituted oxindole (1 equiv), the substituted salicylaldehyde (1.2 equiv) and piperidine (0.1 equiv) in ethanol (1-2 mL/1 mmol) was stirred at 90 C for 3-5 h. After the reaction mixture cooled down, the precipitate was filtered and washed with cold ethanol and diethyl ether, successively. Allowed to dry, the product was used in subsequent reaction without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyloxindole, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Lidan; Ren, Wen; Wang, Xiaoyan; Zhang, Jiaying; Liu, Jie; Zhao, Lifeng; Zhang, Xia; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1071 – 1082;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, molecular formula is C9H7NO2, 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. Computed Properties of C9H7NO2

General procedure: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-74-4, its application will become more common.

Reference:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

1,3-Dihydro-indol-2-one 30a (20.0 g, 150 mmol) was dissolved in sulfuric acid (100 ml, 98%) in an ice-water bath under stirring, and added dropwise with nitric acid (10 ml, 65%-68%) while maintaining the temperature below 0C. Upon completion of the addition, the mixture was stirred for 1 hour at 0C. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ice and filtered after ice-out. The filter cake was washed with water (20 ml×”)), and the resulting solid was recrystallized to obtain the title compound 5-nitro -indol-2-one 30b (25.3 g, yield 92.4%) as an orange solid. MS m/z (ESI): 177.3[M-1]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-2-one, its application will become more common.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20780-72-7, The chemical industry reduces the impact on the environment during synthesis 20780-72-7, name is 4-Bromoisatin, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromoisatin (8.94 g, 39.5 mmol) in anhydrous N, N- dimethylformamide (100 ml_) was added sodium hydride (3.34 g, 86.9 mmol, 60percent dispersion in mineral oil) in portions at 0 0C. The brown reaction mixture was stirred for 30 min followed by the addition of a solution of 2-(bromomethyl)pyridine hydrobromide (10.0 g, 39.5 mmol) neutralized with sodium hydride (1.52 g, 39.5 mmol, 60percent dispersion in mineral oil) in Lambda/,Lambda/-dimethylformamide at 0 0C. The reaction mixture was stirred for 16 h and quenched with water (100 ml_). The reaction mixture was extracted with diethyl ether (3 x 100 mL) and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers was washed with water (5 x 200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether to afford the title compound (10.6 g,85percent) as a brown solid: 1H NMR (300 MHz, DMSO-d6) delta 8.53 (d, 1 H), 7.67 (t, 1 H), 7.30 (t, 2H), 7.25-7.19 (m, 2H), 6.94 (d, 1H), 5.04 (s, 2H); 13C NMR (75 MHz, DMSO-d6) delta 180.5, 157.3, 154.2, 152.3, 149.5, 138.4, 137.5, 128.6, 123.3, 122.3, 121.5, 116.4, 110.3, 45.8.

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2006/113864; (2006); A2;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

4 (^ (0.09111001) Compound 7,36.7840% (0.42111001) of the methylamine solution was added to methanol 2L of the three-necked flask, The temperature of the system was increased to 65 C for 1 h, and 62.2 g (0.49 mil) of oxalic acid and 200 mL of methanol was added dropwise to the system until the pH of the system was stopped at 2-3, At this point the system has a large amount of solid precipitation, the system heated reflux lh, cooled to room temperature, filtration, filter cake with methanol, 50 C vacuum drying to get 34.2g compound 8 (95.1%), 250 C above decomposition

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Sibeiyuan Pharmaceutical Technology Co., Ltd.; Liu Xiaohong; Song Xingchang; Zhang Aihua; Wu Yundeng; (11 pag.)CN103951661; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. Computed Properties of C9H9NO2

Description 13:5-Hydroxyindolin-2-oneTo 5-methoxyindolin-2-one (200 mg, 1.23 mmol) in dry DCM (5 ml), cooled down to 0C, was added a solution of boron tribromide in DCM (1M, 3.5 equiv., 4.3 ml). The reaction mixture was slowly warmed up to room temperature and stirred overnight, then carefully poured into stirring ice-water and stirred for 1 hour. The precipitate was collected by filtration, washed with water, air-dried to give the title compound as a grey solid. The results of NMR spectroscopy set out below indicate the final product was the title compound D13.’H NMR (dmso-d6): 10.06 (1 H, NH, br s), 8.93 (1H, OH. br s), 6.65 (1 H. s), 6.60-6.52 (2H, m), 3.37 (2H, s).13C NMR (dmso-d6): 176.1 , 152.2, 135.5, 126.9, 113.3, 112.3, 109.3, 33.1. MS: (MH+ 41) 191.0.

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

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1914-02-9, These common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, 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.

2d. 3,3-dimethyl-1-(2-nitrophenyl)indoline:; To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175 C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 10% EtOAc in hexane over 30 min as eluting solvent to afford 2d (360 mg, 95%) as an oil. MS (ES) m/z 269 [M+H]+

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1336963-95-1, 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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example Dl, Step 3. To a solution of the 6-bromoindoline-2,3-dione (e.g., 6-bromo-7- fluoroindoline-2,3-dione, 1 equiv) in 1 Nu NaOH (0.14 M) was added H202 (1.8 M) dropwise and the resulting mixture was stirred at room temperature until the reaction was complete (approximately 2 hours). The mixture was filtered and the filtrate was acidified to pH 2 with hydrochloric acid. The precipitate that formed was filtered, washed with water, and concentrated to provide the 2-amino-4-bromobenzoic acid (e.g., 2-amino-4-bromo-3-fluorobenzoic acid).

The synthetic route of 6-Bromo-7-fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEFFERNAN, Michele, L., R.; HARDY, Larry, Wendell; WU, Frank, Xinhe; SARASWAT, Lakshmi, D.; SPEAR, Kerry, L.; WO2012/170845; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem