Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, category: indolines-derivatives

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 ¡ãC (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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.

(1) Preparation of 1-(2-chloroacetyl)-5-nitroindoline5-nitroindoline (16.4g, 100mmol) was dissolved in ethyl acetate (200ml), and then chloroacetyl chloride (9.6ml 120mmol) was slowly added at 40 C. The resulting mixture was heated to 80 C, and reacted for 0.5 hour. The reaction mixture was cooled and filtered by suction. The filtrate was crystallized to produce 1-(2-chloroacetyl)-5-nitroindoline (22g) as a grey solid in a yield of 92%.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; LO, Hoyin; WANG, Aichen; ZHANG, Qian; EP2930167; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

Bromine (1.569 mL, 30.5 mmol) was added dropwise to an ice-cold solution of 5-nitro indoline (5 g, 30.5 mmol) in acetic acid (50 mL), and the mixture was stirred for 1 h. Acetic acid was concentrated under reduced pressure, and the resulting solid was triturated with water to afford the title compound (6 g, 80%) as a yellow solid, which was carried on to the next step without further purification. lU NMR (300 MHz, DMSO-i/6): delta 8.07 (d, J= 2.1 Hz, lH), 7.84 (d, J = 2.1 Hz, 1H), 7.3 (bs, 1H), 3.7 (t, J= 8.7 Hz, 2H), 3.17 (t, J= 8.4 Hz, 2H). ESI-MS m/z = 243 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHEUNG, Mui; TANGIRALA, Raghuram, S.; WO2014/81994; (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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 5-aminoisoindoline-2-carboxylate

tert-Butyl 5-aminoisoindoline-2-carboxylate (200 mg, 0.854 mmol),3,4-dimethoxyphenylboronic acid (155 mg, 0.854 mmol) and monohydrate glycolic acid (63 mg, 0.854 mmol) were dissolved in acetonitrile/DMF (2 mL each). The reaction was heated at 110 0C for 10 min. in a microwave. The reaction was concentrated to an oil and purified with preparatory HPLC to yield 12A (309 mg, 0.721 mmol) in 84% yield. 1H NMR (400 MHz, CDCl3) delta ppm 1.45 – 1.51 (m, 9 H) 3.84 – 3.88 (m, 6 H) 4.48 – 4.56 (m, 4 H) 4.99 (d, J=6.59 Hz, 1 H) 6.36 – 6.55 (m, 2 H). MS (ESI) m/z 429.4 (M+H).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1677-48-1, name is 5,6-Dichloroindoline-2,3-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 1677-48-1, category: indolines-derivatives

General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.

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:
Article; Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur; Indian Journal of Heterocyclic Chemistry; vol. 23; 4; (2014); p. 411 – 418;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

a synthetic process of amlodipine besylate,The difference from Embodiment 1 is thatStep 2 specifically includes:In the reaction tank,Put 350kg of toluene,Stirring,Distilling toluene,After the liquid in the water separator is full,Keep the reflux water for 60 minutes,Sampling to determine water separation,When the water content of the reflux liquid is ?0.2%,Change the reflux to distillation,Distilling off toluene,Stir and cool down,When the temperature inside the tank drops to 45 C,Filling the reaction tank with nitrogen,Continue to cool down to 5 C,40 kg of N-(2-hydroxyethyl)-phthalimide was added with stirring.Then add 20kg of sodium hydride,Plus,Close the lid,Stir at 5 C,38.4 kg of ethyl 4-chloroacetoacetate was taken in the measuring tank.45kg of toluene and mix well,Drop into the reaction tank at 5 CAdd a solution of ethyl 4-chloroacetoacetate in toluene,The dripping time is controlled at 4 hours.Plus,Continue to stir the reaction for 2 hours.Slowly warming up,The temperature of the reaction solution was slowly raised to 38 C within 5 hours.The reaction time is more than 12 hours.Warm up to 51 C and keep warm for 1 hour.Until the reaction is complete,Cooling down,Control the internal temperature of 35 C,Add 61kg glacial acetic acid,Plus,Stirring was continued for 60 minutes to stir the material in the reaction solution evenly.The internal temperature is controlled at 35 C.Add 180kg of water,Plus,Continue to stir for 30 minutes.Stop filling with nitrogen,Stop stirring,Stand still and separate the water layer into the bucket.Transfer the toluene layer to the washing tank,Transfer the water layer to the reaction tank,Add 75 kg of toluene to the reaction tank.Stir,Stand still and separate the water layer into the bucket.Then transfer the toluene layer to the washing tank.Transfer the water layer to the reaction tank,Add 75 kg of toluene to the reaction tank.Stir,Rest,Separate the water layer,Combine the toluene layer into a water wash tank,Add 100kg of 25% salt water to the washing tank.Stir for 15 minutes,Let stand for 30 minutes,Divided into the water layer,Toluene solution of 4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate;The yield of amlodipine besylate was 91.1%, and the purity was 99.3%.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Liu Lijuan; Gao Huanhuan; Yu Yaoying; (13 pag.)CN108456160; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 446292-08-6, The chemical industry reduces the impact on the environment during synthesis 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

100 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione of Formula (I), 1000 ml Methanol and 119 g methyl amine were added to RBF at 25 C. to 35 C. The reaction was heated to 60 C. to 65 C. for 1-2 hours. To the reaction mass oxalic acid (15 g) was added till to pH 5.5 to 6.0 and maintained for 30 minutes. The reaction mass was cooled to 45 to 50 C. and maintained for 30 minutes. The reaction mass was cooled to 25 to 35 C. and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml*2) afforded the oxalate salt of (S)-4-(4-(5-(aminomethyl)-2-oxo-oxazolidin-3-yl)phenyl)morpholin-3-one of Formula (JO).

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CADILA HEALTHCARE LIMITED; Dwivedi, Shriprakash Dhar; Prasad, Ashok; Pal, Daya Ram; Sharma, Mukul Hari Prasad; Jain, Kuldeep Natwarlal; Patel, Naitik Bharatbhai; US2014/378682; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 446292-07-5, The chemical industry reduces the impact on the environment during synthesis 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

200 ml of THF were added to 15.5 g of 2-((2 ?)-2-hydroxy-3-{[4-(3-oxomorpholin-4- yl)phenyl]amino}propyl)- l H-isoindol- l ,3(2H)-dione (14, 0.0392 mol), 19.0 g of Iota , Gamma- carbonyldiimidazole (0.1 176 mol) and 0.05 g of 4-dimethylamino)pyridine. The suspension was stirred and heated to boiling. After ca. 20 minutes from the beginning of boiling the suspension got dissolved, and conversely, after another 5 minutes of boiling a solid substance was formed. Then, the mixture was boiled for another 15 minutes and after that cooled to ca. 40C, which was followed by filtration, washing of the cake with THF (25 ml) and drying. 17.8 of an off-white powder that first melts at 165-175C, then re-crystallizes and melts again at 215 to 217C was obtained. According to HPLC the isolated product was a mixture of 39.6% of the compound (15) and 60.4% of the compound (16), see Fig. 2.

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, (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ZENTIVA, K.S.; HALAMA, Ales; KRULIS, Radim; BRICHAC, Jiri; WO2013/120464; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 74572-29-5, 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 74572-29-5 as follows.

A suspension of copper (I) iodide (88 mg, 0.46 mmol), l-(3-bromophenyl)ethan-l-ol (1.85 g, 9.19 mmol) potassium carbonate (0.65 g, 4.59 mmol) and 5-chloroisoindolin-l-one (0.77 g, 4.59 mmol) in anhydrous A’ A’-d i m e th y 1 fo rm am i dc (3.8 mL) was purged with nitrogen and heated at 150 C for 16 h. The mixture was diluted with 10% ammonium hydroxide solution. General Work-up Procedure 1 was followed. The residue was purified on silica gel (ethyl acetate in hexanes 40% isocratic) to give the title compound as an off-white solid. Yield: 0.42 g (32%).

According to the analysis of related databases, 74572-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 86626-38-2, 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. 86626-38-2 name is 4-Bromoindoline, 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.

Obtained above in MeCN (8mL) 4- bromo-indoline (759mg, 3.81mmol) and the mixture of (Boc) 2O (976mg, 4.48mmol) was stirred at room temperature overnight. After evaporation, the residue was dissolved in ethyl acetate (40 mL), washed with water (3 ¡Á 20 mL) and brine (1x20mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 as a white solid (840 mg, 74%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoindoline, and friends who are interested can also refer to it.

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem