Category: 14192-26-8

Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To N, N-dimethylformamide (1000 ml) were added methyl 2-oxindole-6-carboxylate (100.0 g), benzoic acid methyl ester (78.3 g) and potassium carbonate (180.7 g) were added and stirred at room temperature for 3 hours. N- (4-aminophenyl) -N-methyl-2- (134.5g). After stirring at room temperature for 4 hours, the reaction mixture was poured into water (3000ml), stirred for 30 minutes, filtered and recrystallized from methylene chloride / methanol (10: 4 by volume) and dried to give 257.8g of crystals Compound. (89.7% yield).

The synthetic route of Methyl 2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Kanglisheng Pharmaceutical Development Co., Ltd.; Cheng Gang; (12 pag.)CN104844499; (2017); B;,
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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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 14192-26-8

a) Methyl 3,3-dimethyl-2-oxoindoiln-6-carboxylate To a solution of Mel (7.42 g, 3.27 ml, 52.3 mmol) in DMF (75.0 ml) was added methyl 2- oxoindoline-6-carboxylate (5 g, 26.2 mmol). Once everything was disolved NaH (60 % in mineral oil, 1.05 g, 26.2 mmol) was added and the reaction mixture was stirred for 30 minutes at room temperature. Then again NaH (60 % on mineral oil, 523 mg, 13.1 mmol) was added and stirring was continued for another hour. Again NaH (60 % on mineral oil, 523 mg, 13.1 mmol)was added and stuffing was continued for 15 hours. The reaction was quenched with 1 M aqueous HC1 solution, the mixture was extracted with ethyl acetate and the organic layers were washed with water. The combined organic layers were dried with sodium sulfate, filtered and the obtained solution was concentrated in vacuo. The resulting solid was triturated with diisopropylether, filtered and the collected solid was dried. The title compound was obtained as red solid(4.61 g)MS ESI (m/z): 220.3 [(M+H)i.1H NMR (CDC13, 300 MHz): oe = 7.98 (br s, 1H), 7.78 (dd, J=1.3, 7.8 Hz, 1H), 7.58 (d, J=1.0 Hz,1H), 7.26 (d, J=7.7 Hz, 1H), 3.92 (s, 3H), 1.42 (s, 6H).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
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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 14192-26-8 as follows. Recommanded Product: Methyl 2-oxoindoline-6-carboxylate

In a 250ml reaction flask was added 28.7g of 2-oxindole-6-carboxylic acid methyl ester, 130ml ethanol, stirred open, then added 16.8ml (17.6g) benzaldehyde, 2.97 mL piperidine was heated to 70 -80C, after 2 hours the reaction was allowed to cool to 20 C- 30C, the precipitate was filtered, the filter cake was washed with ethanol, and dried under vacuum 5 hours 50 deg.] C give a yellow solid 40.2g (IV of), yield: 96.0%.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Simbos Pharm Co., Ltd; Li, Yong; Hu, wei; Du, Huanda; Wang, wanqing; Liu, YanHua; (8 pag.)CN105461609; (2016); A;,
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Electric Literature of 14192-26-8, A common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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 stirred solution of methyl 2-oxoindoline-6-carboxylate (10.0 g, 52.33 mmol) in 1,4-dioxane (500 mL) was added selenium dioxide (27.9 g, 261.68 mmol) and the resulting reaction mixture was stirred vigorously at 100 C for 1 h. After completion of the reaction, the reaction mixture was diluted with EtOAc and water and filtered through a bed of celite. The filtrate layers were separated and the organic layer was washed with water and brine, dried over anhydrous Na2S04 and then evaporated under reduced pressure to provide the crude product. This was purified by Comb1-flash using 50% EtOAc in hexanes as eluent to afford methyl 2,3-dioxoindoline-6-carboxylate (3.5 g, 17.06 mmol, 34% yield) as a light yellow solid.

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; CURADEV PHARMA LIMITED; BANERJEE, Monali; MIDDYA, Sandip; BASU, Sourav; YADAV, Dharmendra; GHOSH, Rajib; PRYDE, David; SHRIVASTAVA, Ritesh; SURYA, Arjun; (190 pag.)WO2018/234807; (2018); A1;,
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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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H9NO3

Methyl oxindole-6-carboxylate (300.0 g / 1.5691 mol) was suspended in toluene (900.0 ml) at ambient temperature. Chloroacetic anhydride (282.27 ml / 1.494 eq) was added and the suspension was stirred at reflux for 4 hours. The suspension was cooled to ambient temperature, stirred for 30 minutes and the crystalline product filtered off. The crude product was washed with methyl cyclohexane, ice-cold MeOH and Et20 and dried in vacuum to obtain 358.1 g (85.3 %) of l-(2-chloro-acetyl)-2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid methyl ester.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RATIOPHARM GMBH; TEVA PHARMACEUTICALS USA, INC.; ALBRECHT, Wolfgang; FISCHER, Dirk; JANSSEN, Christian; WO2012/68441; (2012); A2;,
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Application of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-oxoindoline-6-carboxylate (4.08 g) and Mel (6.12 g) in DMF (61 ml) was added at 22 C NaH (1.71 g) over a period of 1.5 h and stirring was continued for 4 h. The mixture was partitioned between aqueous hydrochloric acid (1 M) and EtOAc, the organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane) to give the title compound (0.64 g, 13%) as a brown solid. MS (ESI, m/z): 234.5 [(M+H)+]. The second fraction contained 3,3-dimethyl-2-oxo-2,3-dihydro-lH- indole-6-carboxylic acid methyl ester (3.82 g, 82%) as brown solid. MS (ESI, m/z): 220.5 [(M+H)+].

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

The intermediate from Step D was esterified by heating in acidic methanol overnight. The resulting solution was concentrated under vacuum and the residue was dissolved in hot ethanol (75 mL). Methanol (20 mL) was added to redissolve some material that precipitated as the solution cooled. Sodium nitrite (1.50 g) was added, followed by concentrated hydrochloric acid (5 mL). The reaction was stirred for 2 h, and a further concentrated hydrochloric acid (2 mL) was added. The reaction was stirred overnight. Volatiles were removed under reduced pressure, water added, and the resulting yellow orange product was isolated by filtration and dried under vacuum to give the intermediate (2.1 g) as a yellow orange solid. [MH]+=221.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-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 14192-26-8, Recommanded Product: 14192-26-8

To a stirred solution of methyl 2-oxoindoline-6-carboxylate (5.0 g, 26.16 mmol) in DMF (150 mL) was added Mel (7.42 g, 52.34 mmol) and the mixture cooled to between o and -10 C followed by portionwise addition of NaH (2.19 g, 54.27 mmol, 60% suspension in mineral oil). The whole was allowed to stir at between o and -10 C for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was diluted with water, extracted with EtOAc, and the combined organic layers were washed with brine and dried over anhydrous Na2S04. The dried organics were evaporated under reduced pressure to obtain a crude residue which was purified by Comb1-flash using 35-50% EtOAc in hexanes as eluent to afford methyl 3,3-dimethyl-2-oxoindoline-6-carboxylate (4.4 g, 20.09 mmol, 77% yield) as a light orange solid. LCMS m/z: 220.03 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-oxoindoline-6-carboxylate, and friends who are interested can also refer to it.

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 14192-26-8 as follows. category: indolines-derivatives

Intermediate Ia (4Og) is dissolved in methanol (40OmL) and IM NaOH solution (420 mL) is added. The mixture is heated under reflux for 3 hours. The reaction is then neutralized with IM HCl. The methanol is then removed under reduced pressure and water is added EPO until precipitation commenced. The precipitate is collected via filtration, washed with water and dried under reduced pressure to yield the desired intermediate 2a (37g)

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To the suspension of methyl 2-oxoindoline-6-carboxylate 18[16,17] (50 g, 0.261 mol) in isopropyl alcohol (IPA) (350 ml) was added slowly in sodium methoxide powder (33.8 g,0.626 mol) and stirred for about 15 min. Benzoyl chloride (44 g, 0.313 mol) was added and stirred at 5 to 10 C for about 5 h. After completion of the reaction, the reaction mixture was quenched into ice water (700 mL) and acidified with concentrated HCl up topH 2.0-2.5. The reaction mixture was filtered and washed with water (2 100 mL) and the precipitate is dried to obtain crude product that was recrystallized from acetonitrile (28 mL) to obtain methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylatepure crystalline solid (32 g) (61%) (HPLC purity >97%). The filtrate was evaporated invacuum to get the unreacted methyl 2-oxoindoline-6-carboxylate. M.p.: 216-223 C; IR (KBr, cm 1): 3178, 1711, 1651; 1H-NMR (400 MHz, DMSO): delta3.80 (s, 3H), 7.17 (s, 1H), 7.28-7.31 (m, 2H), 7.46-7.50 (m, 3H), 7.72 (d, 2H, J 6.0 Hz),9.52 (s, 1H), 11.53 (s, 1H); 13C-NMR (100 MHz, DMSO): delta 22.12, 52.41, 101.13, 111.13,119.23, 123.06, 126.65, 127.06, 128.65, 129.21, 132.26, 134.47, 136.99, 166.58, 172.52, and175.80; HRMS (ESI): m/z calcd. For C17H13NO4: 295.0845. Found: 296.0921 [M]1.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Arava, Veerareddy; Gogireddy, Surendrareddy; Synthetic Communications; vol. 47; 10; (2017); p. 975 – 981;,
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