Author: Jessica.F

Electric Literature of 883-44-3, A common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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.

N1-Boc-N4-Nbs-N4-(3-propyl-1-phthalimide)-trans-1,4-diaminocyclohexaneA solution of 310 mg (0.78 mmol) of N4-Boc-N1-Nbstrans-1,4-diaminocyclohexane was dissolved in 20 mL of 1:3 CH2Cl2/benzene together with 254 mg (0.97 mmol) of Ph3P and 127 mg (0.62 mmol) of N-(3-hydroxypropyl)phthalimide. The resulting solution was stirred at 25 C. under argon. To this solution was added 191 L (0.97 mmol) of a 40% solution of DIAD in toluene dropwise. After addition was complete, stirring was continued for an additional 18 hours. The solution was evaporated to dryness and the crude oil purified on silica gel eluting first with 8:2 Hexane/EtOAc then with 1:1 Hexane/EtOAc to give a total of 322 mg (89%) of product as a clear oil (Rf 0.35 (1:1 Hexane/EtOAc

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; Burns, Mark R.; McVean, Maralee; Kennedy, Kevin J.; Yeung, Arthur; Devens, Bruce H.; US2004/235960; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1074-82-4, A common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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.

General procedure: A 500 mL round-bottom flask was charged with4.63 g (0.025 mol) Phthalimide potassium salt, dissolve in 120 mL Anhydrousacetone. 6.9 g (0.05 mol) potassium carbonate and 11.75 g (0.0625 mol) 1,2-Dibromoethanewas added. The solution was heated to reflux for 8 h. The stirring mixture wasallowed to cool, and then was filtered. The solids were washed with 50 mL ofacetone, followed by 50 mL of EtOAc. The filtrate and the washer liquid werepooled and concentrated in a rotary evaporator, then purified by flashchromatography on SiO2 (gradient, 1:6 to 1:4 petroleum ether:EtOAc)to obtain 5.2 g (81.8%) of N-(2-Bromoethyl) phthalimideas a white solid.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
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Reference of 61-70-1, The chemical industry reduces the impact on the environment during synthesis 61-70-1, name is 1-Methylindolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

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, 1-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
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Indoline | C8H9N – PubChem

Reference of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

General procedure: A mixture of aminorhodanine (1 mmol), isatin (1 mmol) and 5 muL of acetic acid in 2mL of distilled ethanol was placed in a cylindrical quartz reactor (Phi = 4 cm). The reactor was introducedinto a monomode microwave (Anton Paar) apparatus, for 5 min at100 C and 50 Watts. The crude reaction mixture was allowed tocool down at room temperature and ethanol (10 mL) or mixture of H2O/EtOH (10 mL) was directly added in the cylindrical quartzreactor. The resulting precipitated product was filtered off and waspurified by recrystallization from ethanol if necessary.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khaldoun, Khadidja; Safer, Abdelmounaim; Boukabcha, Nourdine; Dege, Necmi; Ruchaud, Sandrine; Souab, Mohamed; Bach, Stephane; Chouaih, Abdelkader; Saidi-Besbes, Salima; Journal of Molecular Structure; vol. 1192; (2019); p. 82 – 90;,
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Indoline | C8H9N – PubChem

Related Products of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

An oven-dried flask was charged with oxindole (133 mg, 1 mmol, 1 equiv) before the addition of anhydrous DMF (0.8 M, 1.25 mL) and dibromoethane (94 muL, 1.1 mmol, 1.1 equiv). The solution was then cooled to 0 C before the addition of NaH (60% dispersion in mineral oil, 180 mg, 4.5 mmol, 4.5 equiv) portionwise over 20 min. The mixture was then warmed to r.t. and stirred overnight, then the reaction was quenched with H2O (3 mL) and the mixture was extracted with EtOAc (5 mL). The organic layers were then washed with H2O (2 × 5mL) and brine (2 × 5 mL) and passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc/petroleum ether, 20-40%) to afford the desired product. Yield: 23 mg (14%); red/brown amorphous solid. IR (solid): 3200, 1701, 1684, 1671, 1627, 1474, 1357 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.34 (s, 1 H), 7.19 (t, J = 7.7 Hz, 1 H), 7.01 (t, J = 7.5 Hz, 1 H), 6.96 (d, J = 7.7 Hz, 1 H), 6.83 (d, J = 7.4 Hz, 1 H), 1.76 (d, J = 3.0 Hz, 2 H), 1.54 (d, J = 2.9 Hz, 2 H). 13C NMR (101 MHz, CDCl3): delta = 179.1, 140.6, 131.3, 126.7, 122.0, 118.6, 109.7, 27.4, 19.5. HRMS (NSI): m/z [M + H]+ calcd for C10H10NO: 160.0757; found: 160.0753.

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 150560-58-0, name is 5-Isopropylindoline-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 150560-58-0, Application In Synthesis of 5-Isopropylindoline-2,3-dione

General procedure: A suspension mixture of N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)thiosemicarbazide 2 (2mmol, 0.84g) and appropriate substituted isatin 3a-l (2mmol) and glacial acetic acid (0.02mL) in absolute ethanol was microwave irradiated for 5-15min (depending on substituents on benzene ring of isatins). After irradiating for 1-3min, the suspension mixture became a clear solution. The irradiation was continued in a given time. At the end of reaction process, the precipitate appeared. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature; the color precipitate was filtered with suction. The crude product was recrystallized from 96% ethanol or mixture of toluene-96% ethanol (2:1 in volume) to afford the title compounds of substituted isatin N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl) thiosemicarbazones 4a-l. The spectral (FT-IR, 1H NMR, 13C NMR and ESI-MS or EI-HRMS) data are in good agreement with their structures.

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; Thanh, Nguyen Dinh; Giang, Nguyen Thi Kim; Quyen, Tran Ha; Huong, Doan Thi; Toan, Vu Ngoc; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 532 – 543;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, category: indolines-derivatives

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6?10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Yellow solid, yield: 89percent, m. p.: 153.1?154.9°C, Rf=0.26 (petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.49 (t, J=8.0Hz, 1H), 7.33 (d, J=8.1Hz, 1H), 7.11 (d, J=7.9Hz, 1H), 4.57 (d, J=2.5Hz, 2H), 2.34 (t, J=2.5Hz, 1H).13C NMR (100MHz, CDCl3) delta 179.90, 156.21, 151.10, 138.42, 128.93, 121.74, 116.52, 109.86, 75.36, 73.67, 30.94, 29.53

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 3339-73-9 as follows. Quality Control of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

A solution of 28 (2.000 g, 9.12 mmol), DPPA (1 .966 mL, 9.12 mmol, 1 eq) and TEA (2.543 ml, 2 eq, 1 8.25 mmol) in dry toluene (60 mL) was stirred at rt, under a nitrogen atmosphere. After disappearance of starting materials by TLC (approximately 1 hour), the mixture was refluxed to promote conversion to the isocyanate. After evolution of nitrogen gas had ceased, the reaction mixture was split into half (by volume). 2-aminophenol (747 mg, 1.5 eq, 6.84 mmol) was added to one half of the isocyanate solution and stirred under reflux for 16 hours. On cooling to rt a yellow precipitate formed, which was collected by filtration (suction) and washed with EtOAc. On drying, 867 mg of pale yellow solid was obtained requiring no further purification.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6341-92-0, name is 6-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 6341-92-0, Formula: C8H4ClNO2

Weigh rapamycin (0.05mmol), isatin 3h (0.10mmol) and rhodium octanoate dimer(0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary distillation to give a crude product. The rapamycin analog I-h was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 82%.

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

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (2019); A;,
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Indoline | C8H9N – PubChem

Reference of 446292-07-5, 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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a 2 litre 4 Neck RBF, charge Toluene (830 ml), Compound (IV) (100 gms). Stirr the reaction mass and cool to 10-15C. Charge N,N-carbonyl-diimidazole (82 gms). Reflux the reaction mass at 105-110C for 2 hrs. Cool the reaction mass to 55-60C and charge methanol (170 ml). Cool the reaction mass further to 25-30C and filter. Wash the residue with Methanol (50 gms). Dry the solid under vacuum. Dry Wt: 100 gms (Theoretical yield: 93.80%); Purity: 99.78%

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; MEHTA API PVT. LTD.; KHAN, Rao, Uwais, Ahmad; SONI, Amit Manohar; MALI, Sanjay, Gunda; (29 pag.)WO2016/199027; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem