Category: 14192-26-8

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, Quality Control of Methyl 2-oxoindoline-6-carboxylate

A mixture of compound VI (lOg) and acetic anhydride (40ml) was stirred at about 110C-120C for about 2h. To this reaction mass, triethyl orthobenzoate (35.18gm) was slowly added at about 115-125C for 3h and distilled out low boiler simultaneously at about 120-125C. Then the reaction mass was cooled to about 90C, and concentrated under vacuum to obtain crude compound of formula V.

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Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; NAIK, Samir; SRIVASTAVA, Sachin; PATIL, Pramod; PATIL, Premchand Bansilal; BHIRUD, Shekhar Bhaskar; (34 pag.)WO2019/48974; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

(Roth GJ, et al. J Med Chem.2009;52(14):4466-4480). Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 oC for 8 h. The reaction mixture was allowed to cool to 50 oC and (triethoxymethyl)benzene (2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 oC for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 minutes, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford 974 mg (51%) of title compound.1H NMR (400 MHz, DMSO-d6): delta 8.75 (s, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.49-7.58 (m, 5H), 4.01 (q, J = 7.2 Hz, 2H), 3.87 (s, 3H), 2.44 (s, 3H), 1.35 (t, J = 8.0 Hz, 3H). HRMS m/z found 365.1260, calcd for C21H19NO5 [M]+ 365.1263.

Statistics shows that Methyl 2-oxoindoline-6-carboxylate is playing an increasingly important role. we look forward to future research findings about 14192-26-8.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

A stirred solution of methyl 2-oxoindoline-6-carboxylate (D1) (2.0 g, 10.47 mmol) in acetic anhydride (16 ml) was heated to 130 C under inert atmosphere for 6 h. After complete consumption of the starting material (monitored by TLC), the reaction mixture was cooled to approximately 21 C. The precipitate was filtered, washed with n-hexane (2 x 50 ml) and dried in vacuo to afford compound D2 as a yellow solid (1.5 g, 61.5%).1H NMR (400 MHz, DMSO -de)6 8.66 (s, 1 H), 7.82 (d, J = 8.0 Hz, 1 H), 7.48 (d, J = 8.0 Hz, 1 H), 3.91 (s, 2H), 3.87 (s, 3H), 2.57 (s, 3H)

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

Reference:
Patent; SYNTHIS, LLC; THOMAS-KARYAT, Dori A.; (0 pag.)WO2020/13803; (2020); 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9NO3

Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 C for 8 h. The reaction mixture was allowed to cool to 50 C and (triethoxymethyl)benzene(2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 C for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 min, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford 974 mg (51%) of title compound.

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; Edupuganti, Ramakrishna; Taliaferro, Juliana M.; Wang, Qiantao; Xie, Xuemei; Cho, Eun Jeong; Vidhu, Fnu; Ren, Pengyu; Anslyn, Eric V.; Bartholomeusz, Chandra; Dalby, Kevin N.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2609 – 2616;,
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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C10H9NO3

Sodium hydroxide solution (1N, 20 ml) was added to a solution of methyl 2-oxoindoline-6-carboxylate (2 g, 10.46 mmol, 1.00 equiv) in methanol (20 ml). The resulting solution was stirred for 2 hours at 80 C. The reaction mixture was cooled to 30 C., diluted with 50 ml of H2O and extracted with 2*30 mL of dichloromethane. The aqueous layers were combined and the pH adjusted to 2 with aqueous hydrochloric acid (6 N). The solids were collected by filtration and dried to give the title product 1.28 g (69%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 12.86 (s, 1H), 10.50 (s, 1H), 7.55 (m, 1H), 7.32-7.30 (m, 2H), 3.56 (s, 2H).

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

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); 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. 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. Quality Control of Methyl 2-oxoindoline-6-carboxylate

Sodium hydroxide solution (1N, 20 ml) was added to a solution of methyl 2-oxoindoline-6-carboxylate (2 g, 10.46 mmol, 1.00 equiv) in methanol (20 ml). The resulting solution was stirred for 2 hours at 80 C. The reaction mixture was cooled to 30 C., diluted with 50 ml of H2O and extracted with 2*30 mL of dichloromethane. The aqueous layers were combined and the pH adjusted to 2 with aqueous hydrochloric acid (6 N). The solids were collected by filtration and dried to give the title product 1.28 g (69%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 12.86 (s, 1H), 10.50 (s, 1H), 7.55 (m, 1H), 7.32-7.30 (m, 2H), 3.56 (s, 2H).

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

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); 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. 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

Method 2; 6-Methoxycarbonyl-2-oxindole (10 g; 0,052 mol) is suspended in n-butyl acetate (25 ml) at room temperature. To this suspension a solution of chloroacetic anhydride (12,8 g; 0,037 mol) in n-butyl acetate (25 ml) is added within 3 min. The mixture is heated to reflux for 2 h, then cooled to 85 0C and methyl cyclohexane (20 ml) is added. The resulting suspension is further cooled down to room temperature and stirred for 2 h. The mother liquor is separated and the solid is washed with methanol (400 ml) at ambient temperature. The crystals are dried to afford 12,7 g (91 ,5 %) of the “chlohmide” compound as a slightly yellow solid.

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; WO2009/71523; (2009); 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-oxoindoline-6-carboxylate

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)

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 14192-26-8.

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

These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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. SDS of cas: 14192-26-8

To a solution of methyl 2-oxoindoline-6-carboxylate (17.6 g) in DMF (260 ml) was added Mel (26.1 g) followed by NaH (3.68 g) keeping the temperature at 22 C. After 30 min a second portion of NaH (1.84 g) was added followed after 1 h by a third portion (1.84 g) and stirring was continued at 22 C for 16 h. Water (7 ml) followed by sodium hydroxide (34.5 g) were added and stirring was continued at 45 C for 1 h and at 22 C for 16 h. The mixture was partitioned between TBME and water, the pH of the aqueous layer was adjusted to 3 using aqueous hydrochloric acid (25%) and extracted with dichloromethane. The organic layere was dried and evaporated to give the crude title compound (17.9 g, 95%) as a red solid, which was used without further purification. MS (ESI, m/z): 204.2 [(M-H)”].

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

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

Adding some certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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. 14192-26-8

A mixture of methyl oxindole-6-carboxylate (11.47 g) and acetanhydride (32 ml) was stirredat the bath temperature of 138C; a clear red solution was produced within 10 mm. Thereaction mixture was stirred at 138C for 6 h, then left to stand at 20C for 4 h and the crystallization of the product was completed in 2 h at 10C. The product was filtered off, washed with petroleum ether and finally with glacial methanol. The yield was 12.15 g (87%) of reddish crystals

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 Methyl 2-oxoindoline-6-carboxylate.

Reference:
Patent; ZENTIVA, K.S.; MECA, Ludek; (16 pag.)WO2017/16530; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem