Category: 14192-26-8

14192-26-8, A common compound: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

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.

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; WO2009/71523; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8,Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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) 1,3,3-trimethyl-2-oxoindoline-6-carboxylic acid To a suspension of NaH (60 % on mineral oil, 12.6 g, 314 mmol) in dry THF (260 ml) was added methyl 2-oxoindoline-6-carboxylate (15 g, 78.5 mmol) portionwise during 30 minutes. After gas-evolution ceased Mel (44.5 g, 19.6 ml, 314 mmol) was added dropwise with a syringe- pump during 80 minutes while carefully keeping the temperature between 24 C and 28 C. Thereaction mixture was stuffed for 2 hours at room temperature and then quenched by adding water (5.65 ml, 314 mmol) and then 32 % aqueous NaOH solution (19.6 g, 14.5 ml, 157 mmol) very carefully. The resulting mixture was poured into 100 mL TBME, the layers were separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 25 % aqueous HC1 solution (20m1). The resulting suspension was filtered. The aqueous layer wasback-extracted with dichloromethane, the combined organic layers were dried with sodium sulfate and concentrated in vacuo. The obtained solid was combined with the filtered solid to give the title compound as light red solid (17.7 g).MS ESI (m/z): 220.2 [(M+H)i.1H NMR (DMSO-d6, 300 MHz) oe = 12.98 (br. s, 1H), 7.69 (dd, J=1.0, 7.7 Hz, 1H), 7.55 – 7.41(m, 2H), 3.18 (s, 3H), 1.29 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-oxoindoline-6-carboxylate, its application will become more common.

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8,Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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.

In the four 3000mL round-bottomed flask, fitted with mechanical stirring, reflux condenser, thermometer, nitrogen was added to a 1500mL round bottom flask of toluene, 240g6- methoxycarbonyl-2-oxo-indoline, chlorine 272g acetic anhydride, open stirring, temperature was raised to 80 ~ 90 , the reaction was stirred for 6 hours incubation, naturally fell off the heating 80 , 600ml of cyclohexane was added, and stirring was continued to cool down to room temperature, solid precipitated, suction filtered, the filter cake washed with cold ethanol and dried under vacuum to give 233.6g.Yield: 78%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-oxoindoline-6-carboxylate, its application will become more common.

Reference:
Patent; Nanjing Aide Kai Teng biological medicine limited liability company; Wang, Xuegen; He, Lingyun; Li, Xiaojing; Li, Yiwen; Yu, Yang; Guo, Liqin; (8 pag.)CN105418483; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 14192-26-8

To a stirred solution of methyl 2-oxoindoline-6-carboxylate (1.00 g, 5.23 mmol) in acetic anhydride (10.9 mL, 1 15 mmol) was added (triethoxymethyl)benzene (3.55 mL, 15.7 mmol) and the mixture was stirred at 1 10 C for 4 h. The reaction mixture was cooled to rt and the resulting precipitate collected by filtration. The precipitate was washed with hexanes (100 mL) and dried in vacuo to afford the subtitle compound (?)-methyl 1-acetyl-3- (ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate as a beige solid (1.66 g, 82%); Rl 2.61 min (Method 1); m/z 366 (M+H)+ (ES+).

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, 14192-26-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESPIVERT LIMITED; WALTERS, Iain; BIRCH, Louise; HILL-COUSINS, Joseph; COLLINGWOOD, Stephen, Paul; STEVENSON, Christopher, Scott; (126 pag.)WO2017/109513; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

The 2 – oxo indoline -6 – methyl formate (5g, 0.026 muM), acetic anhydride (20 ml) and the original benzoic acid triethyl ester (29.1g, 0 . 13 muM) are added to a reaction flask, 130 C reaction 6h. The completion of the reaction, the reaction is cooled down to room temperature, filtered, the filter cake is petroleum ether washing, drying, be picture and the solid 7.1g, yield is 75%.

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; Shenyang Pharmaceutical University; Qin Mingze; Gong Ping; Zhang Haotian; Zhao Yanfang; (39 pag.)CN106565682; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 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;,
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

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (3.17 g, 16.6 mmol) and orthobenzoic acid triethyl ester (11.1 g, 49.8 mmol) was suspended in acetic anhydride (15 mL) and toluene (15 mL). the mixture was stirred at 110 C. overnight. After that time, the solvent was removed by evaporation. The residue was triturated with 10 ml petroleum ether, filtered off, and dried at 50 C. under vacuum to give 6 g product. LCMS: m/z=366 (MH)+

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; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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. 14192-26-8

To a suspension of NaH (12.6 g) in THF (260 ml) was added at 22 C methyl 2-oxoindoline-6- carboxylate (15.0 g) over 30 min, which was followed by the addition of Mel (44.5 g) using a syringe-pump over 80 min keeping the temperature between 24 – 28 C and stirring was continued for 2.5 h. A solution of NaOH (6.3 g) in water (20 ml) was added and stirring was continued for 1 h. The mixture was partitioned between water and TBME, the pH of the aqueous layer was adjusted to 1, the suspension was filtered and the residue dried to give the title compound (16.0 g, 93%) as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14192-26-8, its application will become more common.

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