Category: indolines-derivatives

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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Chloroisatin

153.8 mg (0.85 mmol) 6-chloroisatin, 102.1 mg (1.02 mmol) 2,4-pentanedione, 50 mL toluene and 5 mL DMF as solvent, 13.6 mg KMnO4 and 7.5 mg MnO2, and 20 mg strong acid ion exchange resin D001 as catalyst were added to a 100 mL round flask. The mixture was stirred and heated at 115 C. for 9 hours. The reaction was monitored with TLC. When TLC indicated that reaction was complete, heating was removed. The reaction mixture was concentrated, filtered, and washed with toluene to obtain 127.2 mg desired product (compound 8), a yield of 56.9%. 1H-NMR (300 MHz, DMSO-d6) delta (ppm): 10.87 (1H, s), 7.21 (1H, d), 6.85 (1H, s), 6.73 (1H, d), 2.28 (3H, s), 2.23 (3H, s); 13C-NMR (75 MHz, DMSO-d6) delta (ppm): 165.5, 164.1, 153.5, 136.8, 128.4, 126.3, 121.3, 115.9, 106.3, 92.5, 23.9, 11.8; MS (ESI) for (M+Na)+: 286.0.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY; Liang, Chengyuan; Tian, Danni; Jia, Minyi; (11 pag.)US10035808; (2018); B1;,
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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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., name: 5-Methoxyindolin-2-one

5-Methoxyisatin (5.0 g) and 30 mL hydrazine hydrate were heated to reflux for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 1.1 g of insoluble material removed by vacuum filtration and saved. This material proved to be 2-hydrazino-carbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane 1:1 to give 0.7 g of 5-methoxy-2-oxindole as a dirty 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; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-23-1, A common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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 mixture of 5-cyanoindoline (70 mg, 0.487 mmol) and 2′-formylbiphenyl-2,4-dicarboxylic acid 4-ethyl ester 2-methyl ester (0.512 mmol) in 4 mL DCE was stirred for 10 min followed by addition of sodium triacetoxyborohydride (0.155 g, 1.5 eq.). Stirring was continued at rt overnight under N2. Reaction was quenched by addition of 1M NaOH then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over anh. Na2SO4, filtered and evaporated. Flash silica gel chromatography (hexane/ethyl acetate 85:15) provided the product (0.164 g, 76%) as a white, sticky foam. 1H NMR (CDCl3, 300 mHz) delta 8.58 (s, 1H), 8.14 (d, 1H, J=8.4 Hz), 7.36-7.30 (m, 4H), 7.18-7.13 (m, 4H), 6.00 (d, 1H, J=8.4 Hz), 4.44 (q, 2H, J=7.3 Hz), 4.07 (m, 2H), 3.64 (s, 3H), 3.29 (m, 2H), 2.90 (m, 2H), 1.44 (t, 3H, J=7.3 Hz). LRMS (API+) m/z 441.2 (M+H)+ [100].

The synthetic route of 15861-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
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Indoline | C8H9N – PubChem

Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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. HPLC of Formula: C13H16BrNO2

To a 10OmL 3-neck round bottom flask are added 5-bromo-l,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (13.42 mmol; 1.0 equiv), Pd(OAc)2 (0.34 mmol; 0.025 equiv), and P(o-tol)3 (0.67 mmol; 0.05 equiv) and the flask is evacuated and purged with N2 three times. DMF (34 mL), methyl acrylate (14.76 mmol; 1.1 equiv), and Et3N (67.1 mmol; 5.0 equiv) are added and the reaction mixture is heated to 130 C for 15 h. The reaction is cooled to room temperature, diluted with Et2O (200 mL), and the organic layer is washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine. The combined organic extracts are dried (MgSO4), filtered, and concentrated to afford the crude product, which is then purified by silica gel chromatography to yield 5-(2-methoxycarbonyl-vinyl)-l,3- dihydro-isoindole-2-carboxylic acid tert-butyl ester as a yellow solid (1.7 g; 42% yield). 1H NMR (400 MHz, CD3OD): delta 7.68 (d, J= 16 Hz, 1 H), 7.53 (m, 2 H), 7.32 (t, J= 8.0 Hz, 1 H), 6.52 (d, J= 16 Hz, 1 H), 4.64 (d, J= 8 Hz, 4 H), 3.78 (s, 3 H), 1.52 (s, 9 H). MS m/z 305.0 (M+l)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 201940-08-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76954; (2008); A2;,
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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 6-Fluoroindoline-2,3-dione

EXAMPLE 16 Sodium hydride (80% in oil; 0.36 g) was added portionwise to a stirred solution of 6-fluoro-1H-indole-2,3-dione (2 g) in dry dimethylformamide (25 ml). After effervescence had ceased, ethyl bromoacetate (2 g) was added dropwise at 25 to the stirred solution. The orange mixture was stirred at room temperature for 18 hours and then poured into ice-water. The precipitated solid was filtered off, washed with water and dried. 1-(ethoxycarbonylmethyl)-1H-indole-2,3-dione, mp 168-169. (Compound 16).

According to the analysis of related databases, 324-03-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Agrochemicals Limited; US5093364; (1992); A;,
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

These common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, 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. Recommanded Product: (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate

3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H-indol-1-yl}Propyl benzoate(2R, 3R) -mono-tartaric acid salt(Mono-tartaric acid salt of the compound of formula (II)),Potassium carbonate (80 g),And a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C,Stir for 30 min. To the reaction mixture were added 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature,And extracted with 1 L of ethyl acetate and 1.5 L of water.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation. 400 mL of methanol, 100 mL of water and 20 g of KOH were added to the obtained residue. After the mixture was stirred at room temperature for 10 hours,1 L of ethyl acetate and 1 L of water were added and extracted for 10 minutes.The organic layer obtained by layer separation was washed sequentially with 1 L of saturated aqueous solution and 1 L of saturated brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing with 200 mL of ethyl acetate,18 g of oxalic acid was added.The reaction mixture was stirred at 50 for 30 minutes, It cooled to room temperature.600 mL of isopropyl ether was added to the reaction mixture,Stirred for 2 hours, and then filtered.The obtained crystals were washed with 200 mL of isopropyl ether,At 40 for 10 hours to give the titled compound as a dried in vacuo to 88 g. Yield: 82%Purity: 99.5%Impurities (dimer): Not more than 0.1%

The synthetic route of (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dasan Medichem Co., Ltd.; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Kim, Jae Hyung; Aum, Woon Yong; (12 pag.)KR2016/92976; (2016); A;,
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. 71294-03-6, name is 7-Fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 7-Fluoroindolin-2-one

a) 7-Fluoro- 1 ,3,3-trimethylindolin-2-one To a suspension of NaH (8.79 g, 220 mmol) in tetrahydrofuran (100 ml) was added 7- fluoroindolin-2-one (8.30 g, 54.9 mmol) in portion within 20 minutes. The reaction mixture was stirred for 30 minutes. Mel (31.2 g, 13.7 ml, 220 mmol) was added dropwise at 24-27C within 1.5 hours. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was very carefully quenched with 20 ml saturated aqueous ammonium chloride solution at 10-15C, then diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as orange crystals (9.91 g). MS ESI (m/z): 194.3 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 6.99-6.97 (m, 3H), 3.43 (d, J = 2.62 Hz, 3H), 1.37 (s, 6H).

The synthetic route of 71294-03-6 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; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); 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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Chloroisatin

General procedure: To a well-stirred solution of aldehyde 1 or isatin 4 (2 mmol) and tetronic acid 2(4 mmol) in ethanol (5 mL) was added sulfamic acid (20 mol percent) with continuous stirring. With the progress of the reaction, a yellowish solid separated out. Upon completion of the reaction (TLC), the resultant solid was filtered, washed with ethanol and dried. The resultant bis-tetronic acid 3/5 was found to be pure and did not require any further purification.

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; Pandit, Kapil S.; Desai, Uday V.; Wadgaonkar, Prakash P.; Kodam, Kisan M.; Research on Chemical Intermediates; vol. 43; 1; (2017); p. 141 – 152;,
Indoline – Wikipedia,
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Application of 56341-39-0, 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. 56341-39-0 name is 6-Fluoroindolin-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.

At 130 C., 82.5 g of 6-fluoro-2-indolinone (starting material IV) are stirred in 180 ml acetic anhydride for 3 hours. After cooling to room temperature, the precipitate is filtered off with suction, washed with 100 ml of petroleum ether and dried. [0256] Yield: 64.8 g (61% of theory) [0257] Rf value: 0.75 (silica gel, petroleum ether/ethyl acetate=1:1) [0258] C10H8FNO2 [0259] Mass spectrum: m/z=192 [M-H]-

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

Reference:
Patent; Boehringer Ingelheim Pharma GmbH & Co. KG; US2005/43389; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem