Category: 59-48-3

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., Formula: C8H7NO

(e) Preparation of 5-Bromo-2-oxindole. 2-Oxindole (1.3 g) in 20 mL of acetonitrile was cooled to -10 C. and 2.0 g of 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 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

An oven-dried flask was charged with oxindole (133 mg, 1 mmol, 1 equiv) before the addition of anhydrous DMF (0.8 M, 1.25 mL) and dibromoethane (94 muL, 1.1 mmol, 1.1 equiv). The solution was then cooled to 0 C before the addition of NaH (60% dispersion in mineral oil, 180 mg, 4.5 mmol, 4.5 equiv) portionwise over 20 min. The mixture was then warmed to r.t. and stirred overnight, then the reaction was quenched with H2O (3 mL) and the mixture was extracted with EtOAc (5 mL). The organic layers were then washed with H2O (2 × 5mL) and brine (2 × 5 mL) and passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc/petroleum ether, 20-40%) to afford the desired product. Yield: 23 mg (14%); red/brown amorphous solid. IR (solid): 3200, 1701, 1684, 1671, 1627, 1474, 1357 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.34 (s, 1 H), 7.19 (t, J = 7.7 Hz, 1 H), 7.01 (t, J = 7.5 Hz, 1 H), 6.96 (d, J = 7.7 Hz, 1 H), 6.83 (d, J = 7.4 Hz, 1 H), 1.76 (d, J = 3.0 Hz, 2 H), 1.54 (d, J = 2.9 Hz, 2 H). 13C NMR (101 MHz, CDCl3): delta = 179.1, 140.6, 131.3, 126.7, 122.0, 118.6, 109.7, 27.4, 19.5. HRMS (NSI): m/z [M + H]+ calcd for C10H10NO: 160.0757; found: 160.0753.

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:
Article; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
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., HPLC of Formula: C8H7NO

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.

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.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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. Quality Control of Indolin-2-one

Step 1 Oxindole (20.0 g; 0.15 mol) and lithium chloride (21.0 g; 0.49 mol) were suspended in tetrahydrofuran (400 mL) and the mixture cooled to -78° C. n-Butyllithium (120.0 mL; 0.30 mol, 2.5M in hexanes) was added slowly and the mixture was stirred for 20 minutes, then iodomethane (18.7 mL; 0.30 mol) was added. The mixture was warmed to 25° C., stirred overnight and then quenched with saturated aqueous ammonium chloride and diluted with diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography (0-20percent ethyl acetate-hexane) afforded 10.0 g (41percent) of 3,3-dimethyl-1,3-dihydro-indol-2-one as a yellow solid. MS (ESI) m/z 162 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.

Reference:
Patent; Wyeth; US2007/72897; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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. 59-48-3 name is Indolin-2-one, 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.

A stirred mixture of sodium hydride (60%, 31g, 0.79 mol) in dry xylene (500 mL), under a nitrogen atmosphere, was heated to reflux for 30 min. l,3-Dihydro-indol-2-one 16a (100 g, 0.75 mol) was then slowly added via an addition funnel and stirred at reflux for 1.5 hrs. Dimethyl sulfate (104 g, 0.83 mol) was added drop-wise, whereupon the resulting homogeneous solution was refluxed for an additional 2 hrs. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SC>4, and concentrated under reduced pressure to afford l-methyl-l,3-dihydro-indol-2-one 16b (74 g, 67.3%). .HNMR (300 MHz, CDC13) 5 7.23-7.31 (m, 2 H), 7.04 (t, J= 7.5 Hz, 1 H), 6.82 (d, J= 7.8 Hz, 1 H), 3.52 (s, 2 H), 3.21 (s, 3 H).[0270] A suspension of NaH (60%, 70 g, 0.48 mol) in THF (300 mL) was stirred for 10 min at 0 C. Then a solution of l-methyl-l,3-dihydro-indol-2-one 16b (70 g, 2.88 mol) in THF (200 mL) was added at 0 C, and the mixture was stirred for 1 h at room temperature. Benzyl-bis-(2-chloro-ethyl)-amine (129 g, 0.48 mol) was added in portions at 0 C. The mixture was stirred overnight at room temperature, and then was poured into ice-water, extracted with EtOAc. The combined organic layers were dried over IS^SO^ and concentrated under reduced pressure. The residue was purified by column on silica gel (P.E./E.A. 2:1) to give compound 16c (24 g, 16.3%). lH NMR (300 MHz, CDCI3) 5 7.25-7.42 (m, 7 H), 7.02-7.07 (m, 1 H), 6.83 (d, J= 7.5, 1 H), 3.68 (s, 2 H), 3.19 (s, 3 H), 2.74-2.99 (m, 2 H), 2.66-2.72 (m, 2 H), 1.93-2.01 (m, 2 H), 1.79-1.85 (m, 2 H).[0271] To a solution of compound 16c (12 g, 39.2 mmol) in MeOH (100 mL) was added Pd(OH)2/C (1.5 g, 20%>) under N2. The suspension was hydrogenated under H2 (50 psi) at room temperature for 4.5 hrs. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the deprotected spiroindolone product 16d (8 g, 94.5%). ]H NMR (400 MHz, DMSO-rf6) 5 7.46 (d, J= 7.2,1 H), 7.23-7.27 (m, 1 H), 6.96-7.03 (m, 2 H), 3.04-3.14 (m, 5 H), 2.83-2.89 (m, 2 H), 1.61-1.67 (m, 2 H), 1.45-1.51 (m, 2 H). MS (ESI) m/z 217.1 [M+H]+ [0272] 1.0 eq of deprotected spiroindolone 16d (22 mg, 0.10 mmol) was dissolved in anhydrous l,2-dichloroethane:l,2-dimethoxyethane (1.0 mL, 1:1 v/v) and treated with 1.5 N-Carbethoxy-4-tropinone (30 mg, 0.15 mmol), followed by titanium tetraisopropoxide (88 /xL, 85 mg, 0.30mmol). The vial was flushed with nitrogen and stirred at room temperature ~70 h. The reactionwas then diluted with methanol (1.0 mL), cooled in an ice-BbO bath and treated with sodiumborohydride (8 mg, 0.20 mmol). After warming to room temperature and stirring for 90 min, thereaction was further diluted with methanol (2.0 mL), quenched with 1.0 N NaOH (500 juL) andstirred vigorously at room temperature for 10 min. The suspension obtained was centrifuged(3K rpm, 10 min) and the supernatant concentrated under reduced pressure. The residueobtained was dissolved in MeOH:acetonitrile (1250 fiL, 1:1 v/v), filtered, and purified byreverse-phase HPLC (2-40% CH3CN/0.1% TFA gradient over 10 min) to yield productcompound no. 149. LC/MS (10-99%) m/z [M+H]+398.2, retention time 1.93 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Indolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2006/23852; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

1,3-Dihydro-indol-2-one 30a (20.0 g, 150 mmol) was dissolved in sulfuric acid (100 ml, 98%) in an ice-water bath under stirring, and added dropwise with nitric acid (10 ml, 65%-68%) while maintaining the temperature below 0C. Upon completion of the addition, the mixture was stirred for 1 hour at 0C. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ice and filtered after ice-out. The filter cake was washed with water (20 ml×”)), and the resulting solid was recrystallized to obtain the title compound 5-nitro -indol-2-one 30b (25.3 g, yield 92.4%) as an orange solid. MS m/z (ESI): 177.3[M-1]

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

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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 solution of oxindole (4.43 g, 33.3 mmol) in AcOH (35 mL) was added NIS (9 g, 40.0 mmol) at rt. The mixture was stirred for 1.5 hours at which point water (60 mL) was slowly added dropwise, followed by about 5 mL of EtOAc to solubilize impurities. The solid was filtered, washed with a small amount of EtOAc followed by diethyl ether, to give 5-iodo-oxindole (5.4 g, 62%) as a light pink solid clean by proton NMR in DMSO.

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

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
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 59-48-3 as follows. name: Indolin-2-one

5-Acetyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. 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 5-acetyl-2-oxindole as a brown solid. 1H NMR (360 MHz, DMSO-d6) delta10.75 (s, br, NH), 7.83 (d, J=8 Hz, 1H), 7.78 (s, 1H, H-4), 6.88 (d, J=8 Hz, 1H), 3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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. Quality Control of Indolin-2-one

An oven-dried 250 mL round-bottom flask containing indolin-2-one (5.00 g, 36.7 mmol) was fitted with a stirbar and septa, then flushed with nitrogen. Tetrahydrofuran (50 mL) was added and the mixture cooled to -78 . A solution of n-butyllithium in hexane (32.3 mL, 80.7 mmol, 2.5 M solution) was added, and the resulting solution was stirred at -78 for 30 minutes. Next, iodomethane (13.0 g, 91.8 mmol) was added and the mixture stirred at -78 for 10 minutes. The reaction solution was quenched with saturated aqueous ammonia hydrochloride solution. The resulting mixture was extracted with EtOAc (3 x 30 mL) and the combined organic layers were washed with brine (50 mL) , dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on SiO2(0to 50EtOAc/petroleum ether) to afford 3-methylindolin-2-one. MS (EI) calc?d for C9H10NO [M+H]+, 148 found, 148.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); 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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59-48-3

To the solution of 28a (500mg, 3.76mmol) in acetonitrile (8mL) cooled to – 100C, was slowly added N-bromosuccinimide (770mg, 4.33mmol) with stirring. After the addition was complete, the mixture was stirred for Ih at -1O0C, then warmed to O0C for 2h. The resulting precipitate was collected by filtration, washed with water and dried under vacuo to give 28b (513mg, 64.4%).

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; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem