Author: tianli

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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., 39755-95-8

To a suspension of 5-methoxyindoline-2,3-dione (250 mg, 1.41 mmol) in ethylene glycol (1mL) were added hydrazine monohydrate (140 mL) and KOH (79 mg, 1.41 mmol). The mixture was heated under microwave irradiation at 140 C for 5 minutes. Water was added and the mixture was neutralized with 1N HCl. The obtained suspension was extracted 3 times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuum to give 186 mg (81%) as a yellow solid and was used for the next step without further structure determination.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 603-62-3 name is 3-Nitrophthalimide, 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. 603-62-3

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; Lopez-Girona, Antonia; Schafer, Peter H.; Gandhi, Anita; Mendy, Derek; Daniel, Thomas O.; (190 pag.)US9365640; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below.

a) Preparation of 6-bromohexylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,6-dibromohexane (3.95 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80 C. approx. under stirring. Reaction times and process as per Example 4. 2.46 g of pure product were obtained. Yield 66%. Analysis: calcd.: C, 73.02; H, 7.00; N, 6.08. found: C, 72.83; H, 7.25; N, 5.98.

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; Mediolanum Farmaceutici S.p.A.; US5302593; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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

5-Nitro-2-oxindole 2-Oxindole (6.5 g) was dissolved in 25 mL concentrated sulfuric acid and the mixture maintained at -10 to -15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice-water. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid. The crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 6344-05-4, name is 4-Chloroisatin, molecular formula is C8H4ClNO2, 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. 6344-05-4.

80 kg of 2- [4- (1,3-dioxo-2-isoindolinol] phenylbutyric acid prepared in the method of Example 1 and 480 L of acetic acid were charged into a reaction vessel, and stirring was started. A mixture of 64 kg Zinc powder into the reaction tank, atmospheric pressure into the hydrogen chloride gas,The reaction temperature was controlled at 82 C, the reaction started, the reaction time was 1 hour, the reaction liquid all clear. Filter, wash the residue with acetic acid, The filtrate and washings were combined, the solvent was removed under reduced pressure, the residue was poured into appropriate amount of water, stirred and adjusted to pH 5.5-6.5 by ammonia water, dried and centrifuged to give 72.3 kg of indobufen crude product with a yield of 94.7% and a purity of 98.0%

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

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Cao Dongsheng; Han Tao; Zhou Hanjun; Yu Rui; (8 pag.)CN106631974; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, 6326-79-0

To R7 (25.0 g, I I I mmol) in acetonitrile (750 mL) is added Mel (15 mL, 24ltnmol) and KzC03(60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture isfiltered and concentrated. Water and ethyl acetate are added to the residue. The organic layer isextracted twice with water, dried over MgS04 and concentrated. Yield 56%, mlz 240/242 [M+H]+,rt 0.48 min, LC-MS Method XOOl_ 004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, name is Isoindoline, 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. 496-12-8

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1 H, s), 7.36 (1H, br.s), 7.35 (1 H, s), 7.28 (3H, br.s), 6.59 (1 H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+ 332/334.

Statistics shows that 496-12-8 is playing an increasingly important role. we look forward to future research findings about Isoindoline.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

71294-03-6, A common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

7-Fluorooxindole (1.28 g, 8.50 mmol) and lithium chloride (0.899 g, 21.3 mmol) were suspended in 80 mL of THF and cooled to 0 C. n-Butyllithium (8.5 mL, 16.9 mmol) was added slowly, the mixture was stirred for 20 minutes, and then dibromoethane (0.73 mL, 8.5 mmol) was added. The mixture was warmed to 25 C. and stirred for 16 hours. The reaction was quenched with saturated aqueous NH4Cl and diluted with ether. The organics were washed with water, brine, dried over MgSO4, and concentrated. Flash chromatography (10% acetone/hexane) afforded 0.54 g (36%) of 7′-fluorospiro[cyclopropane-1,3′-indol]-2′(1’H)-one as a white solid

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2006/9509; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 1074-82-4

General procedure: A 500 mL round-bottom flask was charged with4.63 g (0.025 mol) Phthalimide potassium salt, dissolve in 120 mL Anhydrousacetone. 6.9 g (0.05 mol) potassium carbonate and 11.75 g (0.0625 mol) 1,2-Dibromoethanewas added. The solution was heated to reflux for 8 h. The stirring mixture wasallowed to cool, and then was filtered. The solids were washed with 50 mL ofacetone, followed by 50 mL of EtOAc. The filtrate and the washer liquid werepooled and concentrated in a rotary evaporator, then purified by flashchromatography on SiO2 (gradient, 1:6 to 1:4 petroleum ether:EtOAc)to obtain 5.2 g (81.8%) of N-(2-Bromoethyl) phthalimideas a white solid.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 15362-40-0

General procedure: A finely ground mixture of chromone-3-carboxaldehyde(1 mmol) and oxindole/indolinone (1-(2,6-dichlorophenyl)-2-indolinone)/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1.2 mmol) was irradiated in microwave oven for 1 min and completion of the reaction was monitored with TLC. Reaction mixture was washed with diethyl ether to get pure compounds 5-10.

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, 15362-40-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shaveta; Singh, Amrinder; Kaur, Matinder; Sharma, Surbhi; Bhatti, Rajbir; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 185 – 192;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem