Month: August 2021

Reference of 88150-75-8, The chemical industry reduces the impact on the environment during synthesis 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, I believe this compound will play a more active role in future production and life.

2-Cyanoethyl 4-(2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy)-3-oxobutanoate Ethyl 4-(2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl) ethoxy)-3-oxobutanoate (8g, 25mmoles) and 3-hydroxypropionitrile (12g, 170mmoles) were heated at 100 under N2 for 10 hours in toluene (100ml) containing a catalytic amount of 4-methylphenylsulphonic acid. Ethyl acetate and water were added; the organic layer was separated, washed with water, dried (MgSO4) and the solvent evaporated. Chromatography on silica eluding with ethyl acetate/petroleum ether (60-80) mixtures gave the title ester (8.9g). M/e 345 M+1+; NMR delta (CDCl3) 4.14 (s,2H), 3.53 (s,2H).

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, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FISONS plc; EP225175; (1988); A3;,
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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Quality Control of 2-Oxoindoline-5-carboxylic Acid

Step 1: Synthesis of 2-oxo-N-[(1R)-1-phenylpropyl]indoline-5-carboxamide A mixture of 2-oxoindoline-5-carboxylic acid (300 mg, 1.69 mmol), (1R)-1-phenylpropan-1-amine (228 mg, 1.88 mmol), HATU (740 mg), 0.16 mL DIPEA in dry DMF (7 mL) was stirred overnight, then concentrated under reduced pressure. The resulting residue was diluted with AcOEt and washed with a saturated aq. solution of K2CO3. The organic layer was dried and concentrated in vacuo. Purification by flash chromatography (Kieselgel, CHCl3:MeOH 15:1) provided intermediate 2-oxo-N-[(1R)-1-phenylpropyl]indoline-5-carboxamide: (340 mg, 68%): NMR (300 MHz, DMSO-d6) delta ppm: 10.59 (s,1H), 8.53 (d,1H), 7.78 (s,1H), 7.76 (d,1H), 7.33 (m,4H), 7.22 (t,1H), 6.85 (d,1H), 4.85 (m,1H), 3.53 (s,2H), 1.79 (m,2H), 0.89 (t,3H); tR: 3.09 min; MS (ESI): m/z (M+H)+ 295; (M+H)-293.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; Oerfi, Zoltan; EP2837626; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, The chemical industry reduces the impact on the environment during synthesis 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of N-arylglycine esters 1 (0.3 mmol) in MeCN(2 mL) were added imides or amides 2 (0.2 mmol) and CuCl(2.0 mg, 0.02 mmol). Then, the reaction mixture was stirred at60 C under air atmosphere until the reaction was completed.Then, the resulting mixture was concentrated under vacuum,and the residue was purified by column chromatography (silicagel, petroleum ether/EtOAc as an eluent) to afford the correspondingproducts 3.(10)

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, 5-Chloroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiao, Li-Jin; Zhu, Zhi-Qiang; Guo, Dong; Xie, Zong-Bo; Lu, Yue; Le, Zhang-Gao; Synlett; vol. 29; 12; (2018); p. 1659 – 1663;,
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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 7-Methylindoline-2,3-dione

General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C ? H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60°C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wei-Hong; Chen, Meng-Nan; Hao, Yi; Jiang, Xin; Zhou, Xiao-Lin; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 278; (2019); p. 124 – 129;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, 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. Safety of 5-Methylisoindoline-1,3-dione

Example 7: Synthesis of 2-r(4′-chlorobiphenyl-4-yl)(methylsulfonyl)amino1-4-(5-methyl- 1,3 -dioxo- L3-dihydro-2H-isoindol-2-yl)butanoic acid (Compound no. 59) (Scheme III, Path G) Step a: Preparation of prop-2-en-l-yl 2-[(4′-chlorobiphenyl-4- yl)(methylsulfonyl)amino]-4-(5-methyl-l,3-dioxo-l,3-dihydro-2H-isoindol-2- yl)butanoate To a solution of hydroxyl derivative (0.250 g, 0.591 moles) in tetrahydrofuran (10 mL) were added triphenylphosphine (0.232 g, 0.88 moles) and 4-methyl phthalimide (0.104 g, 0.65 moles) at 0C. The reaction mixture was stirred for about 15 minutes and diisopropylazodicarboxylate (0.179 g, 0.0.88moles) was added to it at 0C. The reaction mixture was again stirred for about 2 hours at room temperature. After completion, solvent was evaporated to get a crude product which was purified on silica gel column using 30% ethyl acetate: hexane as eluent to get desired compound. Yield: 0.25 g.

The synthetic route of 5-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; PALLE, Venkata P.; SATTIGERI, Viswajanani; SATTIGERI, Jitendra; SONI, Ajay; RAUF, Abdul Rehman Abdul; SIVAKUMAR, R.; REDDY, Ranadheer R.; MUSIB, Arpita; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38944; (2012); 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., 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

Related Products of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 81 3-[4-(2-Diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic Acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid (80 mg, 0.45 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide to give 210 mg (92%) of the title compound as a yellow orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.6 (s, 1H, NH), 7.76 (d, J=8.0 Hz, 1H), 7.66 (s, 1H, H-vinyl), 7.57 (dd, J=1.5 & 8.0 Hz, 1H), 7.40-7.42 (m, 2H), 3.28 (m, 2H, CH2), 2.88 (m, H-piperidine), 2.54 (m, 6H, 3*CH2), 2.44 (s, 3H, CH3), 2.40 (s, 3H, CH3), 1.56 (m, H-piperidine), 0.97 (t, J=6.98 Hz, 6H, N(CH2CH3)2). MS m/z 424 [M+].

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

Reference:
Patent; Pharmacia Corporation; US2003/216410; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, 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 13861-75-1, Application In Synthesis of Spiro[cyclopropane-1,3′-indolin]-2′-one

Bromine (0.15 mL, 3.0 mmol) was added drop-wise to a mixture of spiro[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one (486 mg, 3.05 mmol), 174 muL (3.0 mmol) acetic acid (0.174 mL, 3.0 mmol) and sodium acetate (250 mg, 3.0 mmol) in dry dichloromethane (120 mL). After 4 h, the reaction was washed with 5% sodium thiosulfalte and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 5′-bromospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (0.75 g, 100%) as a white solid. This compound was used without further purification.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Wyeth; US2006/30615; (2006); 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. 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 868066-91-5

(E)-Ethyl 3-(2-methyl-1-oxoisoindolin-5-yl)acrylateA mixture of tri-o-tolylphosphine (0.242 g, 0.796 mmol), ethyl acrylate (1.594 g, 15.92 mmol), 5-bromo-2-methylisoindolin-1-one (1.8 g, 7.96 mmol), Pd(OAc)2(0.089 g, 0.398 mmol), and TEA (2.220 mL, 15.92 mmol) in CH3CN (25.0 mL) was stirred at 80 °C for 3 h. The reaction was filtered and concentrated and the residue was purified by flash column chromatography eluting with petroleum ether/EtOAc (1/5), to afford (E)-ethyl 3-(2- methyl-1-oxoisoindolin-5-yl)acrylate (1.02 g, 3.95 mmol, 49.6 percent yield). LC-MS: m/z 247 (M+H)+1.50 min (ret. time).

The synthetic route of 868066-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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 3676-85-5, Recommanded Product: 3676-85-5

At room temperature,In a 25mL reaction bottle,Join in order3-aminophthalic acid imide(0.5 mmol), diphenylphosphoryl (1 mmol),TEMPO (0.05 mmol), and tetrahydrofuran 48 mmol, 2 mL), mixed evenly,The reaction is then heated to 40 C.The reaction was stirred for 12 hours.After the reaction was completed by TLC, pure water was added.Then add ethyl acetate for 3 times.The extracts are combined and the extract is dried over anhydrous sodium sulfate.The extract was concentrated under reduced pressure in vacuo (0.08 Mpa) to dryness to afford crude material.Then rinse with a mixed eluent of 3:1 by volume of petroleum ether and ethyl acetate.Silica gel column flash column chromatography,Obtaining the product of Example 4o,It was 152 mg of a yellow solid, yield 70%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Qufu Normal University; Wei Wei; Huang Qiang; Lv Yufen; Liu Qishun; (20 pag.)CN109942627; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem