Category: indolines-derivatives

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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H4N2O4

General procedure: A mixture of indole (2 mmol), isatin (1 mmol), SAMSNs (0.06 g), and water (3 ml) was stirred at 60 C for different periods of time as indicated in Table 4. After completion of the reaction (as monitored by TLC), the mixture was cooled to room temperature. The precipitated solid and the SAMSNs were filtered off and dissolved in acetone. After dissolution of the product, the solid catalyst was removed by filtration, and the resulting solution was evaporated under reduced pressure. The pure product was obtained by recrystallization from ethanol.

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; Mehrasbi, Ebrahim; Sarrafi, Yaghoub; Tajbakhsh, Mahmood; Research on Chemical Intermediates; vol. 41; 9; (2015); p. 6777 – 6787;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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 118289-55-7, Recommanded Product: 6-Chloro-5-(2-chloroethyl)indolin-2-one

5-(2-(4-(1,2-benzisothiazol-3-yl)-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one A clean and dry 20-gallon glass lined tank was charged with 19 L of water and 4.44 Kg of sodium carbonate, after the carbonate had dissolved 4.29 Kg (17.5 moles) of 5-(2-chloroethyl)-6-chloro-oxindole and 3.62 Kg (1 6.5 moles) of 1-(1,2-benzisothiazol-3-yl) piperazine were added. The aqueous slurry was heated to reflux and the temperature maintained for 14 hours. When the reaction was complete the solution was cooled to 20 C. and filtered. The wet product was reslurried in 23 L of isopropyl alcohol at room temperature for 2 hours. The product was collected by filtration on 2 large Buchner funnels, each was washed with 3.4 L of fresh isopropyl alcohol. The product was vacuum dried at 30 to 40 C. until no isopropyl alcohol remained, giving 5.89 Kg (86.4% yield) of the desired free base which matched a standard sample by high performance liquid chromatography (HPLC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloro-5-(2-chloroethyl)indolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US5312925; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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.

Step 1: N-Benzyl-N-methyl-2,3-dioxoindoline-5-sulfonamide To a black solution of 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (4.00 g, 16.3 mmol) in 1:1 THF:CHCl3 was added, drop-wise via syringe pump, a solution of N-benzylmethylamine (2.73 mL, 21.2 mmol, 1.3 eq) and N,N-diisopropylethylamine (5.68 mL, 32.6 mmol, 2 eq) in CHCl3 (32 mL) over a period of 1.25 hr. with cooling in an ice bath. After stirring for 50 min. the reaction was allowed to warm to room temperature and stirred for 30 minutes. The reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 98/2 CHCl2/CH3OH to give the analytically pure sample of the title compound as a bright yellow solid (0.18 g, 15% yield). Anal. Calc’d for C16H14N2O4S: C, 58.17; H, 4.27; N, 8.48; Found: C, 57.88; H, 4.36; N, 8.40; MS: (API-ES-) m/z 329 [M-H]. m.p.: 183-185 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dioxoindoline-5-sulfonyl chloride, its application will become more common.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, 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. Application In Synthesis of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

A mixture of phthalic anhydride and beta-alanine were heated to 190-200C in a sealed tube. Stirred for additional 30min at 190-200C after the solids totally melted. The reaction mixture was cooled to room temperature and 50% EtOH/water was added. The resulted suspension was filtered and the white precipitate was further washed with 50% EtOH/water, and then dried under vacuum overnight to give the N- phthaloyl-beta-alanine. Phosphoryl chloride was added to a suspension of N-phthaloyl- beta-alanine and phenylethylamine in acetionitrile. The suspension was stirred for 6h under reflux. Acetonitrile and phosphoryl chloride was removed by vacuum. The reaction mixture was then diluted with DCM and washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtrate was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 20 %) in DCM as eluent to afford the imine compound. Acetic acid and sodium triacetoxyborohydride were added to a solution of imine compound in DCM and stirred for lh at room temperature. The reaction mixture was then washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtration was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 50%) in DCM as eluent to give the amine compound. Cis-l ,2-Cyclohexanedicarboxylic anhydride was added to a solution of amine compound in p-xylene at 50C and stirred for 3h. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography using acetonitrile (0 to 20% with 1% AcOH) in DCM as eluent to give the designed product. Two diastereomers were separated by HPLC using water plus 0.1 %TFA and acetonitrile plus 0.1 %TFA as solvents.

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; THE BROAD INSTITUTE, INC.; HU, Longqin; MAGESH, Sadagopan; CHEN, Lin; LEWIS, Timothy; MUNOZ, Ben; WANG, Lili; WO2013/67036; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 341988-36-1, name is Methyl indoline-6-carboxylate, 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 341988-36-1, Quality Control of Methyl indoline-6-carboxylate

A solution of 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (0.23 g, 1.30 mmol) in pyridine (0.60 mL) was treated with 3,5-dimethylbenzenesulfonyl chloride (0.30 g, 1.47 mmol) and stirred at room temperature for 2 hours. The mixture was diluted with 1N HCl and extracted with dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulphate and evaporated. The residue was taken up in heptane/ethyl acetate 1:1 and filtered. The filtrate was pure 1-(3,5-dimethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester, 0.41 g (92percent), MS (ISP): m/e=346.3 (M+H).

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, Methyl indoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; Sander, Ulrike Obst; US2008/153805; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3484-35-3, The chemical industry reduces the impact on the environment during synthesis 3484-35-3, name is 5-Methylindolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

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, 5-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

954-81-4, name is N-(5-Bromopentyl)phthalimide, 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. Recommanded Product: 954-81-4

A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NAOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed IRA vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDC13) : delta 7.95-7. 98 (m, 2H), 7.83- 7.86 (m, 2H), 7.70-7. 73 (m, 2H), 6.86-6. 89 (m, 2H), 4.00 (t, 2H, J= 6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J= 7.29 Hz), 1. 82-1. 89 (m, 2H), 1.73-1. 81 (m, 2H), 1.50-1. 57 (m, 2H).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-DIMENSIONAL PHARMACEUTICALS, INC.; WO2003/99805; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1677-48-1, name is 5,6-Dichloroindoline-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 1677-48-1, SDS of cas: 1677-48-1

General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.

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, 5,6-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur; Indian Journal of Heterocyclic Chemistry; vol. 23; 4; (2014); p. 411 – 418;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, 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. Safety of 2-(3-Oxobutyl)isoindoline-1,3-dione

In a 10 ml reaction tube, adding phosphine nitrogen ligand L3a (0.31 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laf (43.4 mg, 0.2 mmol) with anhydrous carbonate cesium (6.50 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 af. The conversion is 100%, enantiomeric excess is 93%. 2 Af: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

The synthetic route of 2-(3-Oxobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

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

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem