Indolines-derivatives

Reference of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Combine 5-bromoindoline (3.56 g, 18 mmol) and Et3N (1.92 g, 19 mmol) in CH2Cl2 (40 ml). Cool in an ice bath and add Boc2O (4.14 g, 19 mmol). Allow to warm, stir 2 h and add more Boc2O (0.50 g). Stir 2 h and wash with 1N HCl, then with 1N NaHCO3. Dry (MgSO4) and concentrate. Heat the solid with hexane, allow to cool, and filter to obtain the carbamate as off-white crystals, m.p. 124-6 C

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

Reference:
Patent; Schering Corporation; US2004/220194; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4, 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. 3891-07-4 name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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.

To a stirred suspension of sodium hydride (60 % dispersion in mineral oil, 6.28 g, [157] mmol) [IN N, N DIMETHYLFORMAMIDE (150] mL) under nitrogen at [0C] was added portion wise N (2-hydroxyethyl) phthalimide (2,20 g, 105 mmol). The reaction mixture was then allowed to warm to ambient temperature with stirring for 30 minutes. To a stirred suspension in a separate flask of sodium hydride (60 % dispersion in mineral oil, 6.28 g, 157 mmol) [IN N, N DIMETHYLFORMAMIDE] (150 mL) under nitrogen at [0C] was added portion wise methyl 4-chloroacetoacetate (1,12. 1 ml, 105 mmol). The reaction mixture was then allowed to warm to ambient temperature with stirring for 30 minutes. The two reaction mixtures were then combined portion wise and stirred at ambient temperature under nitrogen for 6 hours. After cooling to [0C,] a further portion of sodium hydride (2.0 g, 50.0 mmol) was added. The mixture was stirred for 10 minutes at [0C,] then a further portion of methyl 4-chloroacetoacetate (3.0 ml, 26.0 mmol) was added. The reaction mixture was then stirred at ambient temperature for 18 hours, then poured onto a mixture of ice and saturated ammonium chloride, and then neutralized with aqueous [HC1] (10 N). The precipitate which formed was filtered off and re-crystallized from ethyl acetate to give a first crop of 3 as a yellow solid. The combined filtrates were extracted with ethyl acetate (3 [X] 300 mL). The combined organic layers were washed with saturated brine (2 [X] 300 mL) and water (300 mL), dried over MgS04 and concentrated under reduced pressure to leave a residue which was purified by column chromatography over silica gel (50 g pre-packed [ISOLUTE] column) using ethyl acetate/hexane (1: 1) as eluent to give a second crop of 3 as a yellow solid, which was combined with the first crop to give methyl 4- ( (2′-hydroxyethyl) phthalimide) [ACETOACETATE] (3) (10.8 g, 34 % yield, 95 % pure by LCMS [AND 1H NMR), 1H NMR] (400 MHz; CDC13): 8 8.13 [(M,] 2H); 7.69 [(M,] 2H); 4.53 (s, 2H); 3.80 [(M,] 2H); 3.70 [(M,] 2H); 3.67 (s, 3H); 3.41 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Hydroxyethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; ARTESIAN THERAPEUTICS, INC.; WO2004/33444; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-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 129487-92-9, Recommanded Product: 129487-92-9

(2) tert-butyl 5-(3,5-dichloro-phenylsulphonylamino)-2,3-dihydro-indole-1 carboxylate; Mass spectrum (ESI+): m/z = 460 [M+NH4]+

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:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/113760; (2008); A2;,
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. 550-44-7, name is 2-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Methylisoindoline-1,3-dione

A 4-N-methylphthalimide/water wet cake (50.0 grams (g) dry weight, containing 10-60% water), resulting from either a mixed acid (H2SC /HNO3) nitration of N- methylphthalimide or an all nitric acid nitration of N-methylphthalimide, was charged to a 1000 mL, single-necked (24/40 joint) round-bottomed flask, equipped with a magnetic stir bar, and means to heat the flask with an external temperature controlled oil bath. The flask was then charged with 367 g of toluene, and enough additional deionized water was added such that the total amount of water present in the flask was equal to 160 g. The amount of water used targeted 20 to 25 wt% of 4NPI with respect to the total weight of 4NPI and water. The reaction mixture was magnetically stirred with an oil bath set temperature of 90C. After the 4NPI had dissolved in the toluene the stirring was stopped, and the lower water phase was removed via pipette. This method of dissolution and separation of the 4NPI toluene phase from the aqueous phase constitutes a purification of the 4NPI as water soluble impurities were extracted from the 4NPI/toluene phase into the aqueous phase. This dissolution/separation method is termed herein the “4NPI Extraction.” The 4NPI toluene solution was then placed on a roto-evaporator, equipped with a hot oil bath to heat the flask, and plumbed to a cold trap connected to a vacuum pump. The flask was rotated in the hot oil bath (temperature controlled at 110C) and the solvent was removed under reduced pressure (<30 mm). Once the majority of toluene had been removed, the flask was allowed to rotate in the oil bath at 110C, 25 mm, for 60 minutes, to afford a dry solid free of toluene and water. The solid was transferred to a glove box inerted with dry nitrogen. The desired dried catalyst (HEGC1, TBAB, or C6B) was added to the dried 4NPI for the bisimide forming reaction. 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 550-44-7. Reference:
Patent; SABIC GLOBAL TECHNOLOGIES B.V.; GUGGENHEIM, Thomas Link; ODLE, Roy Ray; CHAULAGAIN, Mani Raj; (55 pag.)WO2017/117449; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is Indolin-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. HPLC of Formula: C8H7NO

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of the title compound as a brown solid.

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

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

Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

General procedure: A solution of isatins 1 (0.6 mmol), isatylidenyl-chromanones 2 (0.4 mmol), and sarcosine (0.8 mmol) in the 12.0 mL of MeOH at reflux for the specified reaction time and monitored by TLC. Then they were concentrated in vacuo to yield the crude products, which were further purified by column chromatography on silica gel (hexane/EtOAc 8:1 3:1) to give the desired products 3.

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Article; Gong, Yi; Wang, Guan-Lian; Wei, Qi-Di; Chen, Lin; Liu, Xiong-Li; Tian, Min-Yi; Yang, Jun; Feng, Ting-Ting; Zhou, Ying; Synthetic Communications; vol. 48; 9; (2018); p. 1016 – 1024;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20780-72-7, A common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. 4-(o-Tolyl)indoline-2,3-dione Following General Procedure 3,4-bromoisatin (100 mg, 0.44 mmol), potassium 2-methyphenyltrifluoroborate (123 mg, 0.62 mmol), K3PO4 (338 mg, 1.59 mmol) and Pd(PPh3)2Cl2 (31 mg, 0.04 mmol) in THF/H2O (3:1, 3 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid (65 mg, 59percent). deltaH (500 MHz, DMSO-d6) 2.15 (3H, s), 6.93 (2H, m), 7.14 (1H, d, J=7.6 Hz), 7.20-7.26 (1H, m), 7.30 (1H, d, J=7.3 Hz), 7.32-7.37 (1H, m), 7.56 (1H, app t, J=7.9 Hz), 8.84 (1H, br s) deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0 mp 161-162° C.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In an oven dried round-bottomed flask, a solution of the squaramide catalyst I (2 mol%) and 1-acetylindolin-3-one 1 (0.4 mmol) in CH2Cl2(1.0 mL) was stirred at r.t. After 5 min, the o-formyl-(E)-beta-nitrostyrene2 (0.48 mmol) was added and the stirring was continued until the complete consumption of the reactants was observed by TLC.Then the crude mixture was purified by flash chromatography on silicagel using a gradient of n-hexane-EtOAc (9:1 to 1:1) to afford the desired product 3.

The chemical industry reduces the impact on the environment during synthesis 1-Acetylindolin-3-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Mahajan, Suruchi; Chauhan, Pankaj; Loh, Charles C. J.; Uzungelis, Server; Raabe, Gerhard; Enders, Dieter; Synthesis; vol. 47; 7; (2015); p. 1024 – 1031;,
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. 110568-64-4, name is 6-Nitroisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Nitroisoindolin-1-one

Step 4: Synthesis of 5-Amino-2,3-dihydro-isoindol-1-one To a suspension of Fe (1.1 g, 19.6 mmole), NH4Cl (1.5 g, 28 mmole) in a mixture of ethanol/water (30 ml/7 ml) at 80° C. was added a mixture of 5-Nitro-2,3-dihydro-isoindol-1-one (1 g, 5.6 mmole) in 10 ml ethanol. The reaction mixture was stirred at 80° C. for 2 hours. Mixture was cooled down, filtered off, solid was washed with 50 ml ethanol. The filtrate was concentrated, taken into 50 ml ethylacetate, washed with 20 ml water. Organic layer was dried over Na2SO4, filtered and concentrated to give about 900 mg crude. Trituration with methyl t-butylether gave 400 mg pure product, 48percent yield. A 18 ml vial was loaded with a mixture of 30percent H2O2 (1 ml), 3N NaOH (3 ml) and MeOH (2.5 ml). To this mixture 5-Amino-pyridine-2-carbonitrile (450 mg, 3.78 mmole) was added at room temperature. Reaction mixture was stirred at rt for 45 minutes, TLC showed the starting material to be consumed. The mixture was diluted with water and filtered; the solid was washed with water and dried to give 480 mg product, 92percent yield.

According to the analysis of related databases, 110568-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Indolin-2-one

EXAMPLE 483A 5-bromo-1,3-dihydro-2H-indol-2-one A suspension of 1,3-dihydro-indol-2-one (1.3 g, 9.76 mmol) in acetonitrile (20 mL) at -5 C. was treated with N-bromosuccinimide, warmed to room temperature, stirred overnight and filtered to give 1.8 g (87% yield) of the desired product. MS (ESI(+)) m/e 209.9, 211.9 (M-H)-.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/26944; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem