Category: 14192-26-8

14192-26-8, 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.

To the suspension of methyl 2-oxoindoline-6-carboxylate (50 gm, 0.261 mol) in IPA (350 ml) was added slowly SMO-powder (33.8 gm, 0.626 mol) and stirred for about 15 min. Benzyl chloride (44 g, 0.313 mol) was added after completion of the reaction at a reaction temperature of -5 to -10C for about 5hrs. The reaction mixture was quenched into ice-water (700 ml) and acidified with Cone. HC1 (2.0-2.5 ml). Filtered the reaction mixture, washed with water (2X100 ml) and dried the precipitate to obtain crude product which can be recrystallized from acetonitrile (28 ml) to obtain methyl-3-(hydroxy(phenyl)methylene)-2- oxoindoline-6-carboxylate pure crystalline solid (32 gm) (61%) (HPLC purity >97%). The filtrate was evaporated in vacuum to give unreacted methyl 2-oxoindoline-6-carboxylate. MR: 216-223C; IR (KBr, cm”1): 3178, 1711, 1651; 1H-NMR (400 MHz, DMSO): delta 3.80 (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 and 175.80; MS: m/z 294 [M]”1

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

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; ARAVA, Veera Reddy; GOGIREDDY, Surendra Reddy; JASTI, Venkateswarlu; (45 pag.)WO2016/178064; (2016); A1;,
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COA of Formula: C10H9NO3,You could be based in a pharmaceutical company, working on developing and trialing new drugs; or in a public-sector research center, helping to ensure national healthcare provision keeps pace with new discoveries.

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. 14192-26-8

Example 2: Synthesis of the “chlorimide” ( methyl-1 -(chloroacetyl)-2- oxoindoline-6-carboxylate)6-methoxycarbonyl-2- “chlorimide” oxindol; Method 16-methoxycarbonyl-2-oxindole (400 g; 2,071 mol) is suspended in toluene (1200 ml) at room temperature. Chloroacetic anhydride (540 g; 3,095 mol) is added to this suspension. The mixture is heated to reflux for 3 h, then cooled to 80 0C and methyl cyclohexane (600 ml) is added within 30 min. The resulting suspension is further cooled down to room temperature within 60 min. The mother liquor is separated and the solid is washed with ice cold methanol (400 ml). The crystals are dried to afford 515,5 g (93,5 %) of the “chlorimide” compound as a white solid. 1H-NMR (500 MHz, DMSO-d6) delta: 8,66 (s, 1 H, 6-H); 7,86 (d, J= 8,3 Hz, 1 H, 8-H); 7,52 (d, J = 8,3 Hz, 1 H, 9-H); 4,98 (s, 2 H, 15-H2); 3,95 (s, 3 H, 18-H3); 3,88 (s, 2 H, 3-H2). 13C-NMR (126 MHz, DMSO-d6) delta: 174,7 (C-2); 36,0 (C-3); 131 ,0 (C-4); 140,8 (C-5); 115,7 (C-6); 128,9 (C-7); 126,1 (C-8); 124,6 (C-9); 166,6 (C-10); 165,8 (C-13); 46,1 (C-15); 52,3 (C-18). MS: m/z 268 (M+H)+. Anal, calcd. for Ci2Hi0CINO4: C, 53.85; H, 3.77; Cl, 13.25; N, 5.23. Found: C, 52.18; H, 3.64; Cl, 12.89; N, 5.00.

We very much hope you enjoy reading the articles and that you will join us to present your own research about Methyl 2-oxoindoline-6-carboxylate.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71523; (2009); A1;,
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Indoline | C8H9N – PubChem

Application of 14192-26-8, 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. 14192-26-8 name is Methyl 2-oxoindoline-6-carboxylate, 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.

Under the room temperature, 19.1g (100mmol) methyl 2-oxindole-6-carboxylate was suspended in 60 ml toluene. Then add 25.6g (150mmol) chloroacetic anhydride. The mixture at 120 C was heated under reflux for 3 hours, then cooled to 80 C, and in 30 min panega 30 ml methyl cyclohexane, and slowly to room temperature; separating the mother liquor, and with the freezing methanol washing the solid, dry, to obtain white crystal 25.36g, the target compound, the yield is 95%.

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.

Reference:
Patent; Southeast University; Ji, Min; Chen, Hao; Cai, Jin; Liu, Haidong; Li, Rui; (13 pag.)(2016);,
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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., Application In Synthesis of Methyl 2-oxoindoline-6-carboxylate

At room temperature, the 6 – methoxy carbonyl -2 – oxo indoline (50g, 0.26 muM) adding toluene (150 ml) in, slowly adding chloroethyl anhydride (67.5g, 0 . 39 muM). The mixture is heated to reflux, and the stirring reaction 2.5h, then cooling to 80 C, and in the system by adding cyclohexane (100 ml), the resulting solution is cooled to room temperature. Filtering, using toluene and washing the solid, and dried, to obtain white solid 65.8g, yield is 94.2%.

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; Shenyang Pharmaceutical University; Qin Mingze; Gong Ping; Zhang Haotian; Zhao Yanfang; (39 pag.)CN106565682; (2017); A;,
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.

Room temperature, 2-indolone-6- methyl formate(5-2) (4.0g, 20 . 71mmol) suspended in 12 ml in toluene of, the chloroactic anhydride (5.4g, 30 . 95mmol) into the above-mentioned suspension, heating reflow 3h, cooling to 80 C, 30 min by adding methyl cyclohexane (6 ml), stirring suspension of cooling to room temperature, filtered to obtain crude products, with cold methanol (4 ml) washing, drying the white solid obtained 5.155g (93.5%), i.e. compound 1-cholroacetyl- 2-indolone-6- methyl formate (6-2).

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

Reference:
Patent; Sichuan University; Chen, Yuanwei; Xie, Yongmei; Wei, Yuquan; (32 pag.)CN104003925; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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 a yellow solution of methyl 2-oxoindoline-6-carboxylate (6.24 g, 31.7 mmol, Eq: 1) and methyl iodide (9.08 g, 4 ml, 64 mmol, Eq: 2.02) in dry dimethylformamide (90.5 ml) was added portionwise a suspension of NaH in mineral oil (60% w/w, 2.54 g, 63.4 mmol, Eq: 2) over 1.5h while controlling the exothermicity with a water bath. The reaction mixture was carefully poured on an icecooled mixture of -1 1 g sodium hydrogenocarbonate, water (150 mL) and ethyl acetate(150 mL). The resulting mixture was extracted with ethyl acetate and the organic layers were washed with brine. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo.The residue was triturated with heptane ethyl acetate 1:1 and the precipitate was filtered and washed with heptane ethyl acetate 1:1. The solid was dried in vacuo to afford the desired product as a light brown solid (5.026 g, 72%).MS (mlz) = 218.1 [M + H].

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (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. Product Details of 14192-26-8

Methyl 2-oxindoline-6-carboxylate (20 g, 105 mmol) was charged to the reaction vessel. The vessel was equipped with thermometer, stirrer and condenser. Toluene (100 ml, 5 vol) was added followed by acetic anhydride (90 ml, 954 mmol) and the mixture was heated to reflux (115-118 C ). Reflux was continued for 18 hours and a sample was analyzed by HPLC for methyl 2-oxindoline-6-carboxylate (nmt 2.0 a-%). When the methyl 2-oxindoline-6-carboxylate was consumed 40 ml (2 vol) of solvent was distilled off followed by addition of fresh toluene (40 ml, 2 vol). Trimethyl orthobenzoate (53.9 ml, 314 mmol) was added to the boiling reaction during a couple of minutes maintaining the temperature above 110 C . After the addition was complete distillation began and the temperature of the reaction mixture was above 120 C. Eight volumes (160 ml) of solvents were distilled of after which the reaction temperature was adjusted between 110-115 C. The reflux was continued for two hours and precipitation of methyl (E)-l -acetyl-3 -(methoxy(phenyl)methylene)-2- oxoindoline-6-carboxylate began during the reaction. According to HPLC- chromatogram 93.6 % conversion was achieved. The reaction mixture was allowed to cool to room temperature during 5 hours, and then further cooled to 0 C and stirred for two hours at 0 C. The precipitate was filtered and washed with EtOAc (2 x 20 ml, 2 x 1 vol) and dried in vacuum oven at 60 C for 16 hours to obtain the product (33.99 g, 90.85 %, 98.36 a-%) as tan powder

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

Reference:
Patent; FERMION OY; PIISOLA, Antti; TOIS, Jan; (13 pag.)WO2019/97112; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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.

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
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, Formula: C10H9NO3

Intermediate Ia (9.Og, 47mmol), 2-ethoxybenzaldehyde (6.60 mL, 47mmol) and piperidine (2mL) are dissolved in methanol (100 mL) and heated under reflux for 2 hours. The solution is allowed to cool to room temperature and the resulting precipitate is collected via filtration and washed with methanol and then ether and dried under reduced pressure to give the desired product 1-01 (13.4g).

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

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