Tag: M.W=200-300

Electric Literature of 3335-98-6, 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. 3335-98-6, name is 1-Phenyloxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

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

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. SDS of cas: 675109-26-9

O2O3] &bromoisoindolin4-orse (1050 mg, SM m.mol% copper powder (32 mg, 0.5 mmol) and methylamine (40% in F120, 2.7 mL) were placed in a pressure vess& and the sealed reaction was heated at 105 C overnight. The reaction mixture was poured into ethyl acetate (150 niL) and washed with saturated NH4CI solution. The organic layer was dried over sodium sulfate, filtered and concenflted. The volatile was removed in vacua and the residue was then purified by silica gel chromatography eluting with MeOH and dichloromethane Rf 0.2, 5% MeOH in DCIVO to afford 300mg of the title compound. MS (m/z): 163.13 [M+H]t HPLC retention time 0.17 mm (248% acetonitrile: water with 0.05% trifluoroacetie acid). ?H NMR (400 MHz, dmso) 8 8.28 (s 1K), 7.20 (d, J= 8.2 Hz, 1H), 6.75 (dd, J 8.2, 2.2 Hz5 lH), 6.68 (d, J= 2.1 Hz, 1K), 5.83 (d, J 5.0 Hz, IH), 4.15 (s, 2K), 2.66 (d, J= 5,1 Hz, 3Ff).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven, S.; CHOU, Chien-Hung; LINK, John, O.; TSE, Winston, C.; WO2015/130964; (2015); A1;,
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Electric Literature of 169037-23-4, 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. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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.

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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Indoline | C8H9N – PubChem

Application of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The synthetic route of 2-(4-Bromobutyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
Indoline – Wikipedia,
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Reference of 3335-98-6,Some common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, molecular formula is C14H11NO, 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 1Preparation of Compound 1 Sodium hydride (50% dispersion in mineral oil, 0.235 g, 4.8 mmol) was added to a stirred solution of 1,3-dihydro-1-phenyl-2H-indol-2-one 1a (2.0 g, 9.6 mmol) in dimethylacetamide (25 mL). To the resulting solution was added bis(2-chloroethyl)amine (1.7 g, 9.6 mmol) in benzene (25 mL) at room temperature. The resulting reaction was heated to about 50 C. and allowed to stir at this temperature for 0.5 hours, then additional sodium hydride (0.235 g, 4.8 mmol) was added and stirring was continued for 2 hours. The reaction mixture was cooled to room temperature, diluted with benzene and treated with water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to provide compound 1b.

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

Reference:
Patent; McCormick, Kevin D.; Aslanian, Robert G.; Mangiaracina, Pietro; Berlin, Michael Y.; De Lera Ruiz, Manuel; Boyce, Christopher W.; Chao, Jianhua; Ting, Pauline C.; Zheng, Junying; Rosenblum, Stuart B.; US2011/166124; (2011); A1;,
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Electric Literature of 667463-64-1, The chemical industry reduces the impact on the environment during synthesis 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

1-3.1 (397 mg, 1.65 mmol) and hydrazine hydrate (1 mL, 20.6 mmol) are heated to 100 C for 1 h and at 125 C for 1 h. To the cool reaction mixture DCM and water are added and the aqueous layer extracted twice with DCM. The combined organic layers are washed with brine, dried, concentrated and the residue purified via column chromatography (using solvent mixture cyclohexane / EA = 3:1). Yield 65%. m/z 226 [M+H]+, m/z 224 [M+H]-, rt 0.58 min, LC-MS Method b.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-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. Formula: C14H13NO3

Preparation of 2-amino-6-phthalimido-4,5,6,7-tetrahydrobenzothiazole via 4-(phthalimido)-cyclohexanone; 1.0 Kg of 4-(phthalimido)-cyclohexanol was added in 20.0 L of acetone at 250C to 350C. The reaction mixture was cooled to 50C to 100C and treated with chromic acid solution. 0.2 L of isopropanol was added and stirred for 30 min. The reaction mixture was filtered and washed with acetone (1.0 L). The filtrate was treated with 0.4 kg sodium bicarbonate at 250C to 350C and stirred for 1 h. The reaction mass was again filtered, washed with acetone (1.0 L). Excess of acetone was distilled under vacuum. The residue was treated with 0.5 L ethanol followed by distillation of ethanol under vacuum. The reaction mass was cooled and treated with 3.36 L ethanol at 450C to 250C while gradual cooling. The reaction mixture was further cooled to 150C to 200C and treated with 0.22 L of bromine and 0.43 Kg of thiourea under stirring for 1 h. The reaction mixture was heated to reflux at 750C to 780C for 6 hrs. The reaction mixture was cooled and stirred for 1 hr at 50C to 100C. The product was isolated by centrifuge, washing with ethanol 0.66 L and drying under vacuum at 500C to 550C. (yield: 0.70 Kg).

The synthetic route of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2008/41240; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 200049-46-3,Some common heterocyclic compound, 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, molecular formula is C8H6BrNO, 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.

7-bromo-2,3-dihydro-lH-isoindol-l-one (5.7 g, 26.88 mmol) was added to sulfuric acid (60 ml) at 0C. The resulting mixture was stirred at 0C for 30 minutes. Then N-iodosuccinimide (9.07 g, 40.32 mmol) was added in one portion and the resulting suspension stirred at 0C for 2 hours. The reaction mixture was poured into ice water, causing a precipitate to form. The precipitate was extracted with ethyl acetate (3 x 200 ml). Both organic and aqueous phases contained precipitates. The organic phase was washed with 10% Na S C (200 ml) to remove excess iodine. The organic layer was dried with sodium sulphate, filtered and evaporated to afford 7-bromo-6-iodo-2,3-dihydro-lH-isoindol-l-one (7.2 g, 79%) as a white solid. 1H NMR (400 MHz, DMSO, 30C) 4.11 (2H, s), 7.43 (1H, d), 7.83 (1H, d), 8.90 (1H, s). m/z: ES+ [M+H]+ = 338.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-2,3-dihydro-isoindol-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; LAMONT, Scott, Gibson; KEMMITT, Paul, David; GOLDBERG, Frederick, Woolf; (158 pag.)WO2019/215203; (2019); A1;,
Indoline – Wikipedia,
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Application of 65435-04-3, A common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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 suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL of pyridine at 80-90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solid was dissolved in 90 mL of 2.5 N sodium hydroxide and stirred at 70-80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

The synthetic route of 65435-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 101207-45-8,Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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.

Add 251 mg of 2- (4-methylbenzyl) isoindolin-1,3-dione (1 mmol), 12 mg of potassium methoxide to a glass test tube with magnetons, add 2 ml of isopropanol under nitrogen protection, add 2 microliters of 0.01M catalyst (S / C = 50,000), filled with 4 MPa hydrogen, and reacted at 40 C for 24 hours. After the reaction, the reaction mixture was naturally cooled to room temperature, and the hydrogen gas was carefully released. The celite was filtered, and the organic solvent was removed from the filtrate to obtain 249 mg of the product in a yield of 98%

The synthetic route of 101207-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South University of Science and Technology of China; Ma Baode; Shao Panlin; Wu Chao; Wang Jiang; Zhang Xumu; (12 pag.)CN110746342; (2020); A;,
Indoline – Wikipedia,
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