Month: June 2021

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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C14H15NO3

General procedure: A round-bottom flask was charged with the corresponding alcohol (1.0 equiv) followed by the addition of Et2O (0.1 M). The solution was cooled to 0 C. Next, oxalyl chloride (2.0 equiv) was added dropwise. The homogeneous reaction mixture was allowed to warm to ambient temperatureand stir for 1-18 h. The reaction was cooled to 0 C and quenched by slow addition of H2O (100.0 equiv). After stirring for 1 h at room temperature, the resulting mixture was transferred to a separatory funnel, and the aqueous layer mixture was extracted with three portions of Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure affording the desired oxalic acid. All the oxalates were used without 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; Gonzalez-Esguevillas, Maria; Miro, Javier; Jeffrey, Jenna L.; MacMillan, David W.C.; Tetrahedron; vol. 75; 32; (2019); p. 4222 – 4227;,
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. 21857-45-4, name is 5-Methoxyindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Methoxyindoline

General procedure: The mixture of xylene (1.0 mL), substrate (0.3 mmol), and rGO (100 w%) was stirred at 100 C for 12 h under O2 atmosphere. After the reaction, the mixture was diluted with AcOEt and water. The organic phase was concentrated under reduced pressure, and purified by column chromatography with silica gel.

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 21857-45-4.

Reference:
Article; Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; 1; (2016); p. 21 – 23;,
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Indoline | C8H9N – PubChem

Related Products of 667463-64-1, 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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Related Products of 41663-84-7, These common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-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.

EXAMPLE 6 To a reaction vessel were added 4-nitro-N-methylphthalimide (0.51 g, 0.00248 mol), sodium hydrogen sulfide (0.07 g, 0.00125 mol), biphenyl (0.204 g, 0.00132 mol), triethylamine (0.2 ml, 0.0014 mol), tetrabutylphosphonium bromide (0.15 g, 0.00044 mol) and dry toluene (40 ml). The reaction mixture was allowed to proceed at reflux (approximately 145 C.) for 18 hours. The reaction mixture was sampled and tested by HPLC which indicated a yield of 4,4′-bis(N-methylphthalimide)sulfide of 10% (0.04 g).

Statistics shows that 2-Methyl-5-nitroisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 41663-84-7.

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of Methyl 4-12-(PHTHALIMIDO) ETHOXY] ACETOACETATE (XV) A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 60 mL of tetrahydrofuran under nitrogen atmosphere. 3.14 g sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 10 g OF N-(2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 7.48 g ethyl 4-chloroacetoacetate in 25 mL of tetrahydrafuran was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 5 mL ethanol. The mixture was then poured into 100 mL of 1N hydrochloric acid solution in crushed ice and 150 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 50 mL of 5 wt. % OF NHC03 solution, then with 100 mL of water, dried over 5 G ofMgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 10 ML of hexane to remove the mineral oil to give 8.87 g of methyl 4-[2-(PHTHALIMIDO) ethoxy] aceto acetate as a light brown product (yield 55%, rel. compound purity > 95%). IR (KBR. CM~L . : 2995 and 1716.-1H-NMR (CDC13) 8 7.80 (dd, 2H), 7.70 (dd, 2H), 4.11 (s, 2H), 3.87 (t, 2H), 3.75 (T, 2H), 3.61 (s, 3H), 3.44 (s, 2H). 13C-NMR (CDC13) 6 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 52.8, 46.0, 37.4.

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, 2-(2-Hydroxyethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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. category: indolines-derivatives

isatin(1.0 mmol) was added to a 50 mL dry round bottom flask in turn.O-iodophenylacetonitrile (1.0 mmol), 4-hydroxycoumarin (1.0 mmol),Catalyst 3e (5 mol%), palladium dichloride (5 mol%),KOH (20 mol%), DMSO 3 mL, mix well, stir at 110 C,After the reaction was completed (TLC tracking), an appropriate amount of water was added and extracted with ethyl acetate.The organic phases are combined, and the excess solvent in the system is distilled off under reduced pressure.The crude product was separated by column chromatography (V petroleum ether: V ethyl acetate = 1:1 gradient elution) to give the title compound 12b in a yield of 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39603-24-2, its application will become more common.

Reference:
Patent; Jiangsu Normal University; Chen Wen; Yuan Rui; Cui Hao; Ren Xuanxuan; Zhou Shengliang; Wan Yu; Wu Hui; (19 pag.)CN109305970; (2019); A;,
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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 32692-19-6

N,N-Dimethyl-2-(5-nitroindolin-1-yl)ethanamine (2) A solution of compound 1 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in an orange mixture. It was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (877 mg, 6.09 mmol) resulting in a dark red mixture. The reaction was heated to 90 C. and stirred for 1.5 hours. After allowing the reaction to cool to room temperature, water (80 mL) was added, and the reaction was extracted into ethyl acetate (3*25 mL). The combined organic layers were washed with water (2*15 mL) and then with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was subjected to flash chromatography on silica gel:CH2Cl2 and then 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brownish/red solid (400 mg, 56% yield). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.1, 8.7 Hz, 1H), 7.79 (d, J=2.1 Hz, 1H), 6.49 (d, J=9.0 Hz, 1H), 3.72 (t, J=8.7 Hz, 2H), 3.39 (t, J=6.6 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 2.44 (t, J=6.3, 2H), 2.18 (s, 6H).

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; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 435273-55-5,Some common heterocyclic compound, 435273-55-5, name is 4-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

2-methyl-l-oxoisoindoline-4-carbaldehyde: To a solution of 4-bromo-2- methylisoindolin-l-one (200mg, 0.89 mmol) in THF (3 mL), n-BuLi (0.78 mL, 1.95 mmol) was added to the solution at -78 C. After 30 minutes, DMF (0.273 mL, 3.57 mmol) was added to the solution. After 1 hour, the reaction was warmed up. Diluted with EtOAc and washed with brine. The organic layer was dried over sodium sulfate, and concentrated. The product was purified by chromatography on silica gel (eluent: EtOAc/hexanes) to yield the product after lyophilization from water / MeCN.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-Hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (604 pag.)WO2017/7689; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A reaction mixture of compound 19-21 (2.35 mmol),compound 14-18 (2.14 mmol) and 2 drops of piperidine was stirred at RT for 3 h. The precipitate was filtered off and dried. The crude compound was purified by column chromatography using ethyl acetate in dichloromethane (13%) to afford the desired products (4, 22-32).

The chemical industry reduces the impact on the environment during synthesis 5-Methylindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dai, Hou-Ling; Gao, Li-Xin; Yang, Ying; Li, Jing-Ya; Cheng, Jia-Gao; Li, Jia; Wen, Ren; Peng, Yan-Qing; Zheng, Jian-Bin; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7440 – 7443;,
Indoline – Wikipedia,
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Application of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

EXAMPLE 61a 4-(6-Chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester A suspension of 6-chlorooxindole (0.71 g, 4.24 mmol) (Cresent Chem.), (3-oxo-butyl)-propyl-carbamic acid tert-butyl ester (1 g, 4.69 mmol) (Tyger Sci.), and pyrrolidine (0.1 g) (Aldrich) in 2-propanol (15 mL) was heated at 90 C. for 2 days. The mixture was allowed to cool to room temperature. The solvent was removed and the residue was purified by chromatography to give 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester as a brown solid. (Yield: 1.36 g, 88%).

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; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem