Category: 59-48-3

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. Computed Properties of C8H7NO

EXAMPLE I 5-acetyl-2-indolinone 171 g (1.28 mol) of aluminium chloride are cooled in 500 ml of 1,2-dichloroethane in the ice bath. Then 78 g (1.1 mol) acetyl chloride are added dropwise, so that the temperature does not exceed 10 C. After 1 h 71.3 g (0.53 mol) 2-indolinone (1,3-dihydro-indol-2-one) are added in 4 batches and the temperature is kept at 10-12 C. The reaction mixture is allowed to come up to ambient temperature slowly overnight. Then the solution is slowly added to 1 kg of ice with vigorous stirring. The slurry is with diluted 1 l water and stirred for another 30 min. Then the precipitate is suction filtered. Yield: 80.9 g (86.3% of theory) Rf=0.36 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C10H9NO2 (MG=175.19) Mass spectrum: m/z=174 (M-H)-

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203104; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 59-48-3, 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 59-48-3 as follows.

3-Methyl-1,3-dihydro-indol-2-one A solution of oxindole (665 mg, 5.0 mmol) in THF (10 ml) was treated dropwise with n-BuLi (4.4 ml, 11.0 mmol) at -78 C., stirred for 30 min. at -78 C. To the reaction methyliodine (2 ml) was added dropwise at -78 C. The resulting solution was warmed up to room temperature. The mixture was quenched with water. The reaction solution was partitioned between ethylacetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered and concentrated under vacumm. Purification on silica gel with 30% ethyl acetate/hexane to provide the title compound (630 mg, 86%). MS (DCI/NH3) m/e 148 (M+1)+.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); 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. 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. Product Details of 59-48-3

5-(Bromo)-1,3-dihydro-indol-2-one A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96 %) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

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

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: Indolin-2-one

Step 1: Spiro[cyclopropane-1, 3? -indoline] -2?-one An oven dried round bottom flask equipped with dropping funnel capped with rubber septum and nitrogen inlet and set in a removable dry ice-acetone bath was purged with nitrogen, and charged with an indolin-2-one (30.0 g, 225.3 mrnol), diisopropylamine (66.3 mL, 470.3 mmol) and dry THF (400 mL)The content of flask was cooled to -20C. The starting material was partially dissolved in THF at room temperature, re-precipitated as reaction mixture, and cooled down. A solution of n-BuLi as a 2.5 M solution in hexanes (360.5 mL, 901.2 mmol) was slowly transferred to dropping funnel viacannula, and then slowly added to the reaction mixture. The rate of addition was adjusted to keep the temperature of reaction mixture at -20 to -30C. When the addition was complete7 the dry ice bath was removed and replaced with regular ice bath, and the temperature was maintained at 0C for1 h. To the resulting reaction mixture was carefully added a solution of l,2-dibromoethane (58.24 mL, 675.9 mmol) in THE? (60 niL) . The resulting reaction mixture was then stirred 18 h at RT. The reaction mixture was then quenched with brine (40 mL), con.HC1 (60 mL) and water (180 mL). The resulted mixture(pH 2-3) upon standing separated into two layers. The Organic layer was removed, and the aqueous layer was extracted with ethyl acetate (200 niL) . The combined organic layer was then washed successively with sat. aq. sodium bicarbonate solution, water and brine, dried over sodium sulfate and evaporated under reduced pressure to obtain a solid. The solid thus obtained was washed with heptane:water (1:1) to give the title compound as a solid (35 g, 97.6%)MS(ESI)m/z: 160.1 [M+l]; ?HNMR (400 MHz, DMSO-d6) : 5 1.50-1.55(m, 2H) , 1.44-1.48 (m, 2H) , 6.88-6.97 (m, 3H) , 7.14 (t, J =8.4 Hz, 1H), 10.6 (s, 1M).[0229]

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DESHPANDE, Anil M.; BARAWKAR, Dinesh; PATIL, Santosh; BANKAR, Digambar; (178 pag.)WO2016/88903; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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.

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.

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

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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.

5-Bromo-2-oxindole 2-Oxindole (1.3 g) in 20 mL acetonitrile was cooled to -10 C. and 2.0 g N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of the title compound.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Pharmacia Corporation; US2003/216410; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;; ; Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Sun, Li; Wei, Chung Chen; Shirazian, Shahrzad; Liang, Congxin; Vojkovsky, Tomas; Nematalla, Asaad S.; Hawley, Michael; US2002/156292; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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 59-48-3 as follows.

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is 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 59-48-3, category: indolines-derivatives

To a stined solution of oxindole (20 g, 150 mmol) in 100 mL of Conc. H2S04 at -15 Cwas added fuming HNO3 (9.47 g, 150 mmol) drop wise. The reaction mixture was allowed tomaintain the temperature at -15 C for 0.5h. After completion of the reaction, the reaction mixture was poured into crushed ice. The yellow solid precipitate out which was isolated by filtration and dried under vacuum (13 g, 48%). ?H-NMR (300 MHz, DMSO-d6) oe ii (s, 1H), 8.20-8.10 (m, 2H), 7.00 (d, J=8.4 Hz, 1H), 3.6 (s, 2H).LC-MS: mlz 177 (M-H).

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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UJJINAMATADA, Ravi Kotrabasaiah; SAMAJDAR, Susanta; HOSAHALLI, Subramanya; ABBINENI, Chandrasekhar; (70 pag.)WO2018/109650; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is 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 59-48-3, Formula: C8H7NO

Concentrated nitric acid (9.31 g, 0.096 mol) was added in drops over 60 min and at 0 C. to a solution of indolin-2-one (13.3 g, 0.100 mol) in concentrated sulfuric acid (67 mL), and the resultant dark-brown solution was then stirred at this temperature for 1 h. The reaction mixture was then poured over ice and sucked away. The residue was washed again with water and dried, then recrystallized from isopropanol. 5-nitroindolin-2-one in the form of golden, shiny sheets was obtained (12.28 g, 69%). fp: >300 C. 1HNMR (300 MHz, d6-DMSO): delta=3.61 (s, 2H, H2), 6.97 (d, 1H, H7), 8.05 (d, 1H, H6), 8.05 (s, 1H, H4), 8.15 (d, 1H, H6), 11.03 (bs, 1H, NH). 13C NMR (100 MHz, DMSO): 35.9 (C2), 109.2 (C7), 120.3 (C4), 125.1 (C6), 127.2 (C9), 142.0 (C5), 150.6 (C8), 177.0 (C2)

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; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); 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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of Indolin-2-one

EXAMPLE I 5-acetyl-2-indolinone 171 g (1.28 mol) aluminium chloride in 500 ml 1,2-dichloroethane are cooled in the ice bath. Then 78 g (1,1 mol) acetylchloride are added dropwise, so that the temperature does not exceed 10 C. After 1 h 71.3 g (0.53 mol) 2-indolinone (1,3-dihydro-indol-2-one) are added in 4 batches and the temperature is maintained at 10-12 C. The reaction mixture is left overnight to come up slowly to ambient temperature. Then the solution is slowly added to 1 kg ice with vigorous stirring. The slurry is diluted with 1 l water and stirred for another 30 min. Then the precipitate is suction filtered. Yield: 80.9 g (86.3% of theory) Rf=0.36 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C10H9NO2 (MW=175.19) Mass spectrum: m/z=174 (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; Boehringer Ingelheim International GmbH; US2005/209302; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem