Category: indolines-derivatives

Reference of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatin (1 mmol), dicarbonyl compound 1 (1 mmol),dicarbonyl compound 2 (1 mmol) and SSLP (0.1 g, 4.8 mol%) wasadded to a 25 mL canonical flask contained water (5 mL) and was stirred at 80 C for appropriate time. After completion of the reac-tion as indicated by TLC, the reaction mixture was filtered and washed with acetone (25 mL, two times) to separate the catalyst.The obtained organic phase was evaporated and the residue was recrystallized from ethanol to obtain the pure products.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Khalafi-Nezhad, Ali; Shahidzadeh, Elham Shaikhi; Sarikhani, Samira; Panahi, Farhad; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 1 – 8;,
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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide, A new synthetic method of this compound is introduced below., Safety of N-(6-Bromohexyl)phthalimide

Triphenylmethanethiol (11.90 g, 43.08 mmol) was suspended in DMSO (40 mL). DBU (7.41 mL, 49.55 mmol) and 6-bromohexylphthalimide (13.32 g, 42.94 mmol) were added, and the mixture was allowed to react for approximately 15 min. The reaction mixture was partitioned between ethyl acetate (700 mL) and 0.1 M HCl (200 mL). The aqueous phase was extracted with ethyl acetate (3*50 mL), and the combined organic fractions were washed with NaHCO3 sat. (80 mL) and brine (80 mL), dried over MgSO4, filtered and concentrated. The crude yellow oil was recrystallized from n-heptane/ethyl acetate. The intermediate 6-(S-Trityl-)mercaptohexylphthalimide was obtained as a white solid (13.3 g, 26.4 mmol, 62%).

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; SANOFI-AVENTIS DEUTSCHLAND GMBH; RAU, Harald; CLEEMANN, Felix; HERSEL, Ulrich; KADEN-VAGT, Silvia; LESSMANN, Torben; WEGGE, Thomas; US2015/258207; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature 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: A mixture of secondary amine (1.0 mmol), calcium carbide (0.20 g, 2.5 mmol), aldehyde (3 mmol), cuprous chloride (0.01 g, 0.1 mmol) and water (0.05 mL, 3 mmol) in DMSO (3 mL) was stirred at 100 C under N2for 4 h. The reaction was monitored by TLC. After reaction completion, the resulting mixture was filtered to remove the solid, and the liquor was extracted with ethyl acetate (3 × 10 mL) and washed with saturated brine (3 × 10 mL). The resulting organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using petroleum ether and ethyl acetate (v/v 10:1) as the eluent.

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; Fu, Rugang; Li, Zheng; Journal of Chemical Research; vol. 41; 6; (2017); p. 341 – 345;,
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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H4BrNO2

Example 8 Heck reaction of 4-Bromophthalic imide with 1 ,7-Octadien (Heck condition) 1 g 4-Bromophthalic imide (6.167 mmol), a two-fold excess 1 ,7-Octadien (12.33 mmol) and the catalysator system were solved in 50 ml DMF. The catalysator system consisted of Palladiumacetate (5 mol-% to Imide: 0.31 mmol), 0.92 mmol Triphenylphosphane and 6.17 mmol Triethylamin. The solution has been heated for 24 h at 150 C (Control of reaction progress via thin layer chromatography with CH2CI2: n-Hexane [5:1]). From the resulting dark brown solution the solvent was removed by reduced pressure. The obtained viscous brown raw product was solved with 80 ml CH2CI2 and washed three times (3 x 200 ml) with a saturated H20/NaCI solution. After that the CH2CI2-phase was dried with MgS04 and the solvent was removed by reduced pressure. The viscous brown product (1 ) was dried under constant vacuum. Yield : quant. IR : v 1772, 1717 (s, Imide) cm 1 MS / ESI : 401.14972 m/z (M+H+)

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; DENTSPLY DETREY GMBH; KLEE, Joachim, E.; RETZMANN, Nils; RITTER, Helmut; SZILLAT, Florian; WO2014/114446; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6, A common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol %), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.

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; Yu, Jiangxia; Shen, Tianhua; Lin, Yan; Zhou, Yongbing; Song, Qingbao; Synthetic Communications; vol. 44; 14; (2014); p. 2029 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3783-77-5, 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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 50 g of 2- (3-oxobutyl) isoindoline-1,3-dione, 14.3 g of ethylene glycol and 7.4 g of p-toluenesulfonium tetrahydrate were dissolved in 500 ml of anhydrous toluene and treated with a water separator Reflux for 24 hours. After completion of the reaction, the reaction system was saturatedNaHCO3 aqueous solution 500 ml twice. The aqueous phase was extracted twice with 500 ml of ethyl acetate. The organic phase is combined with anhydrous sulfur Dried over sodium carbonate, and the solvent was distilled off under reduced pressure to obtain a distillation residue which was recrystallized from ethanol to give 45 g of a yellow solid: 2- (2-(2-methyl-1,3-dioxolan-2-yl) ethyl) isoindoline-1,3-dione, yield: 74.8%.

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; Wuhan Yao Ming Kant, Immanuel New Drug Development Co., Ltd.; Yu Lingbo; Wang Ruile; Zhou Qiang; Xu Xueqin; Zhang Dawei; Bai Youyin; Chen Dongzhi; Gao Mingfei; Yao Baoyuan; Han Huaxin; Fu Xinyu; Ma Rujian; (5 pag.)CN106939001; (2017); A;,
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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Methylindoline

General procedure: Diphenyliodonium triflate (2a, 0.1 g, 0.23 mmol, 1.1 equiv) was charged in a vial and sealed with a septum. After adding TFE (3mL), indoline (1a, 0.024 mL, 0.21 mmol) was added dropwise slowly to the solution, which was then heated to 70 C for 14 h.After the solution was cooled to r.t., the mixture was diluted with H2O and sat. NaHCO3. The aqueous phase was extracted several times with CH2Cl2. The organic phase is washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel, eluting with cyclohexane-CH2Cl2 (2:1, v/v) giving 34 mg(83%) of 3a as a colorless solid.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Riedmueller, Stefan; Nachtsheim, Boris J.; Synlett; vol. 26; 5; (2015); p. 651 – 655;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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 solution of 5-nitroindoline (1 g, 6.09 mmol) in dry DMF (20 ml), K2CO3 (1.094 g, 7.92 mmol) and benzyl 2-bromoacetate (1.242 ml, 7.92 mmol) were added, and the resulting suspension was heated at 65 C. for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was removed. The residue was purified by flash chromatography on silica gel column (DCM:petroleum ether=60:40) affording benzyl 2-(5-nitroindolin-1-yl)acetate (0.782 g, 2.504 mmol, 41% yield). MS/ESI+ 312.9 [MH]+.

Statistics shows that 5-Nitroindoline is playing an increasingly important role. we look forward to future research findings about 32692-19-6.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, A new synthetic method of this compound is introduced below., Safety of 5-(2-Chloroacetyl)indolin-2-one

REFERENCE EXAMPLE 1 5-Chloroacetyloxindol (45 g) was added to 180 ml of pyridine and the mixture was stirred at 80 C. for an hour. After completion of reaction, the mixture was allowed to cool and crystals which precipitated were collected by filtration and washed with acetone. The crystals were then recrystallized from methanol to give 5-alpha-pyridinumacetyloxindolchloride. The compound was added to 600 ml of water containing 12.7 g of sodium hydroxide and stirred at 70-80 C. for 30 minutes. After completion of reaction, the resultant solution was allowed to cool down and acidified with concentrated hydrochloric acid. Crystals which precipitated were collected by filtration and washed with water. The crystals were then recrystallized from a mixture of dimethylformamide (DMF) and water to give 28 g of 5-carboxyoxindol. m.p.: >300 C.

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; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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 102359-00-2 as follows. SDS of cas: 102359-00-2

EXAMPLE 15 To a solution of 0.88 g of 5-carboxyoxindol in 10 ml of DMF was added under ice-cooling 0.82 ml of triethylamine, and 0.77 ml of isobutyl chloroformate was added thereto subsequently. The mixture was stirred at the same temperature for 1 hour. Then, 1.1 g of 1-benzylpiperazine was added thereto, and the mixture was stirred at room temperature overnight. After the reaction was completed, DMF was removed under reduced pressure, and to the residue was added an aqueous sodium hydrogencarbonate solution and extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was distilled off under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent: methylene chloride_methanol=50:1) and recrystallized from isopropyl alcohol to give 0.7 g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. m.p.: 151-153 C.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem