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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 32692-19-6

N,N-Dimethyl-2-(5-nitroindolin-1-yl)ethanamine (2) A solution of compound 1 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in an orange mixture. It was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (877 mg, 6.09 mmol) resulting in a dark red mixture. The reaction was heated to 90 C. and stirred for 1.5 hours. After allowing the reaction to cool to room temperature, water (80 mL) was added, and the reaction was extracted into ethyl acetate (3*25 mL). The combined organic layers were washed with water (2*15 mL) and then with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was subjected to flash chromatography on silica gel:CH2Cl2 and then 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brownish/red solid (400 mg, 56% yield). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.1, 8.7 Hz, 1H), 7.79 (d, J=2.1 Hz, 1H), 6.49 (d, J=9.0 Hz, 1H), 3.72 (t, J=8.7 Hz, 2H), 3.39 (t, J=6.6 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 2.44 (t, J=6.3, 2H), 2.18 (s, 6H).

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; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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. category: indolines-derivatives

isatin(1.0 mmol) was added to a 50 mL dry round bottom flask in turn.O-iodophenylacetonitrile (1.0 mmol), 4-hydroxycoumarin (1.0 mmol),Catalyst 3e (5 mol%), palladium dichloride (5 mol%),KOH (20 mol%), DMSO 3 mL, mix well, stir at 110 C,After the reaction was completed (TLC tracking), an appropriate amount of water was added and extracted with ethyl acetate.The organic phases are combined, and the excess solvent in the system is distilled off under reduced pressure.The crude product was separated by column chromatography (V petroleum ether: V ethyl acetate = 1:1 gradient elution) to give the title compound 12b in a yield of 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39603-24-2, its application will become more common.

Reference:
Patent; Jiangsu Normal University; Chen Wen; Yuan Rui; Cui Hao; Ren Xuanxuan; Zhou Shengliang; Wan Yu; Wu Hui; (19 pag.)CN109305970; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of Methyl 4-12-(PHTHALIMIDO) ETHOXY] ACETOACETATE (XV) A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 60 mL of tetrahydrofuran under nitrogen atmosphere. 3.14 g sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 10 g OF N-(2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 7.48 g ethyl 4-chloroacetoacetate in 25 mL of tetrahydrafuran was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 5 mL ethanol. The mixture was then poured into 100 mL of 1N hydrochloric acid solution in crushed ice and 150 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 50 mL of 5 wt. % OF NHC03 solution, then with 100 mL of water, dried over 5 G ofMgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 10 ML of hexane to remove the mineral oil to give 8.87 g of methyl 4-[2-(PHTHALIMIDO) ethoxy] aceto acetate as a light brown product (yield 55%, rel. compound purity > 95%). IR (KBR. CM~L . : 2995 and 1716.-1H-NMR (CDC13) 8 7.80 (dd, 2H), 7.70 (dd, 2H), 4.11 (s, 2H), 3.87 (t, 2H), 3.75 (T, 2H), 3.61 (s, 3H), 3.44 (s, 2H). 13C-NMR (CDC13) 6 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 52.8, 46.0, 37.4.

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, 2-(2-Hydroxyethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 41663-84-7, These common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-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.

EXAMPLE 6 To a reaction vessel were added 4-nitro-N-methylphthalimide (0.51 g, 0.00248 mol), sodium hydrogen sulfide (0.07 g, 0.00125 mol), biphenyl (0.204 g, 0.00132 mol), triethylamine (0.2 ml, 0.0014 mol), tetrabutylphosphonium bromide (0.15 g, 0.00044 mol) and dry toluene (40 ml). The reaction mixture was allowed to proceed at reflux (approximately 145 C.) for 18 hours. The reaction mixture was sampled and tested by HPLC which indicated a yield of 4,4′-bis(N-methylphthalimide)sulfide of 10% (0.04 g).

Statistics shows that 2-Methyl-5-nitroisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 41663-84-7.

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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.

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); 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. 21857-45-4, name is 5-Methoxyindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Methoxyindoline

General procedure: The mixture of xylene (1.0 mL), substrate (0.3 mmol), and rGO (100 w%) was stirred at 100 C for 12 h under O2 atmosphere. After the reaction, the mixture was diluted with AcOEt and water. The organic phase was concentrated under reduced pressure, and purified by column chromatography with silica gel.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 21857-45-4.

Reference:
Article; Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; 1; (2016); p. 21 – 23;,
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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H15NO3

General procedure: A round-bottom flask was charged with the corresponding alcohol (1.0 equiv) followed by the addition of Et2O (0.1 M). The solution was cooled to 0 C. Next, oxalyl chloride (2.0 equiv) was added dropwise. The homogeneous reaction mixture was allowed to warm to ambient temperatureand stir for 1-18 h. The reaction was cooled to 0 C and quenched by slow addition of H2O (100.0 equiv). After stirring for 1 h at room temperature, the resulting mixture was transferred to a separatory funnel, and the aqueous layer mixture was extracted with three portions of Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure affording the desired oxalic acid. All the oxalates were used without further purification.

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; Gonzalez-Esguevillas, Maria; Miro, Javier; Jeffrey, Jenna L.; MacMillan, David W.C.; Tetrahedron; vol. 75; 32; (2019); p. 4222 – 4227;,
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 61-70-1 as follows. Application In Synthesis of 1-Methylindolin-2-one

To 10 ml schlenk bottle adding N – methyl -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N – methyl -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N – methyl isatin, I – 2, the isolation yield is 73%,1

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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.

Example 8 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (82 mg, 0.2 mmol), 2-oxoindoline-6-carboxylic acid (36 mg, 0.2 mmol), EDCI (76 mg, 0.4 mmol) and N-methylimidazole (50 mg, 0.6 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by preparative TLC (Silica gel, 20 cm*20 cm, separated by EtOAc, eluted by DCM_MeOH=1:20, v/v) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide (25 mg, 23.5%). 1H NMR (300 MHz, DMSO): delta 10.52 (s, 1H), 9.56 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 7.90 (brs, 1H), 7.48-7.46 (m, 2H), 7.28-7.25 (m, 2H), 6.93-6.90 (m, 1H), 4.54 (brs, 1H), 3.77-3.34 (m, 11H), 2.50-2.34 (m, 1H), 2.07-1.99 (m, 2H). LC-MS: 532 [M+H]+, 530 [M-H]-, tR=1.35 min. HPLC: 97.39% at 214 nm, 97.05% at 254 nm, tR=4.54 min.

Statistics shows that 2-Oxoindoline-6-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 334952-09-9.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

24566-79-8, name is N-(6-Bromohexyl)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: 24566-79-8

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 synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; Sprogoe, Kennett; Cleemann, Felix; Hersel, Ulrich; Kaden-Vagt, Silvia; Lessmann, Torben; Rau, Harald; Wegge, Thomas; (61 pag.)US9265723; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem