Author: Jessica.F

Application of 39755-95-8, The chemical industry reduces the impact on the environment during synthesis 39755-95-8, name is 5-Methoxyisatin, I believe this compound will play a more active role in future production and life.

The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflux for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 1.1 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrazinocarbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid.

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 20870-79-5, name is 5-Nitroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6N2O3

5-Nitro-1,3-dihydro-indol-2-one 30b (3.56 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) to the solution at room temperature. The reaction mixture was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 5-amino-1,3-dihydro-indol-2-one 30c (2.04 g, yield 68.9%) as a white solid. MS m/z (ESI): 149.4[M+1]

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

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

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
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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 7699-18-5 as follows. Computed Properties of C9H9NO2

General procedure: Compounds 8 and 10 were prepared from azo coupling of aryldiazonium salts 3a,b with5-methoxyindolin-2-one 2, previously described [24]. Aryldiazonium salts were prepared startingto corresponding amines (21.5 mmol) in HCl 6N (11 mL) with water solution (7.5 mL) of sodiumnitrite (23 mmol). This solution was added to solution of indol-2-one (21.5 mmol) and sodium acetate(43 mmol) in methanol (59 mL) at 0 C. The resulting precipitate was filtered and purified.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco; Molecules; vol. 23; 7; (2018);,
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Indoline | C8H9N – PubChem

Reference of 480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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 5 mL microwave tube was cliargedwimisomdolin-l-one (0.2544 g, 1 .911 mmol), cesium caib onate ( 1.245 g.3.82 mmol) and N-memyl-2-pynOlidinone (9.55 mL) to give a colorless solution. Bmmoa etaldehyde dimethyl acetal ( 1.125 mL, 9 5 mmol) was added . The tu e was sealed, and the reaction mixture was heated in a Eiotage Creabrat 160 *C fcr 60 minutes fined hold time. The reaction mixture was partitioned between ethyl acetate and water. The organic layerwas washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The reaction mixture was purified b y flas h chromatography (20-70 % ethyl acetate :heptane) to provide ab lown oil (0.179 g, 42 % yield).

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
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Electric Literature of 3485-84-5, These common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, 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: Furan-3-carbaldehyde oxime (2) (300 mg, 2.7 mmol, 1.0 equiv) was mixed with 1-fluoro-4-vinylbenzene (0.39 ml, 3.24 mmol, 1.2 equiv) in dry THF (10 ml). To this mixture, sodium hypochlorite solution (12 ml) was added. Subsequently, the reaction constituents were stirred at room temperature under nitrogen for approximately 16 h. On completion of the reaction, solvent was evaporated. Extraction was carried out using ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated to obtain the crude compound. The latter was then purified by silica gel column chromatography to obtain the pure compound.

Statistics shows that N-Vinylphthalimide is playing an increasingly important role. we look forward to future research findings about 3485-84-5.

Reference:
Article; Balachandran, Sarala; Gadekar, Pradip K.; Parkale, Santosh; Yadav, Vitthal N.; Kamath, Divya; Ramaswamy, Sneha; Sharma, Somesh; Vishwakarma, Ram A.; Dagia, Nilesh M.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 5; (2011); p. 1508 – 1511;,
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Indoline | C8H9N – PubChem

Electric Literature of 20780-72-7,Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.

SYNTHETIC PREPARATION 13; Synthesis of 4-bromo-3-(3-hydroxy-6-methoxypyridin-2-yl)-1 ,3-bis( hydroxy methyl )-1 ,3- dihydro-2H-indol-2-one A. Synthesis of 4-bromo-3-hydroxy-3-(3-hvdroxy-6-methoxypyridin-2-yl)-1 ,3- dihydro-2/-/-indol-2-oneTo a pale yellow solution of 6-methoxypyridin-3-ol (7.16 g, 57.2 mmol) in anhydrous tetrahydrofuran (100 ml.) was added isopropylmagnesium chloride (28.6 mL, 57.2 mmol, 2.0 M solution in tetrahydrofuran) at 0 0C. The reaction solution was stirred for 30 min followed by the addition of solid 4-bromoisatin (10.3 g, 45.8 mmol) in portions. The reaction mixture was stirred at ambient temperature for 2 days. The reaction was quenched with 10percent aqueous hydrochloric acid solution (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether to afford 4-bromo-3-hydroxy-3-(3- hydroxy-6-methoxypyridin-2-yl)-1 ,3-dihydro-2H-indol-2-one (10.7 g, 67percent) as a pale yellow solid: mp 172-175 0C; 1H NMR (300 MHz, DMSO-d6) delta 10.61 (s, 1H), 9.41 (s, 1 H), 7.10 (d, J = 8.0 Hz, 2H), 6.99 (d, J = 8.1 Hz, 1 H), 6.81 (d, J = 7.6 Hz, 1 H), 6.77 (br, 1 H), 6.68 (d, J = 8.6 Hz, 1 H), 3.77 (s, 3H); 13C NMR (75 MHz, DMSO-Cf6) delta 176.5, 155.5, 145.9, 139.4, 131.6, 128.9, 127.2, 125.6, 118.9, 111.8, 111.1 , 109.3, 53.8; MS (ES+) mlz 353.2 (M + 1 ), 351.2 (M + 1 ).

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

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2008/46049; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 346-34-9, 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. 346-34-9, name is 4-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .In analogy to intermediate 1 A, 300 mg (1.82 mmol) 4-fluoro-1 H-indole-2,3-dione was heated with 900 muL (9.08 mmol) 1 -cyclopropylethanone, 112 mg (2.00 mmol) potassium hydroxide, 208 muL (3.63 mmol) acetic acid and 209 mg (2.54 mmol) sodium acetate in 3 mL water for 6 h at 150 C in the microwave. The reaction mixture was quenched with 10% hydrochloric acid solution and filtered. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to obtain 120 mg (0.52 mmol, 29%) of the desired title compound after drying.1 H NMR (400 MHz, DMSO d6): delta (ppm) = 1.10 – 1.17 (m, 4 H), 2.40 – 2.47 (m, 1 H), 7.52 – 7.60 (m, 2 H), 7.93 (s, 1 H), 8.35 – 8.41 (m, 1 H,) 13.98 (br. s, 1 H).

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-Fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, 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.

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H4FNO2

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .1 H NMR (300 MHz, DMSO d6): delta (ppm) = 8.14 (dd, 1 H), 8.21 (d, 1 H), 8.32 (s, 1 H), 9.09 (d, 1 H), 14.50 (br. s. , 1 H)._n analogy to intermediate 1 A, 200 mg (1.21 mmol) 6-fluoro-1 H-indole-2,3-dione was heated with 217 muL (2.42 mmol) 1 ,1 ,1 -trifluoroacetone, 75 mg (1.33 mmol) potassium hydroxide, 139 muL (2.42 mmol) acetic acid and 139 mg (1.70 mmol) sodium acetate in 2 mL water for 2 h at 80 C in the microwave. As the conversion was not complete further 217 muL (2.42 mmol) 1,1 ,1 -trifluoroacetone was added to the reaction mixture and heated again for 1 h at 80 C in the microwave. Once again 217 muL (2.42 mmol) 1 ,1 ,1-trifluoroacetone was added and the reaction mixture was heated a third time for 1 h at 100 C in the microwave to obtain 227 mg (0.88 mmol, 72%) of the desired title compound after aqueous work-up.1 H NMR (300 MHz, DMSO d6): delta (ppm) = 7.83 – 7.93 (m, 1 H), 8.10 (dd, 1 H), 8.26 (s, 1 H), 8.90 (dd, 1 H), 14.51 (br. s. , 1 H).

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 324-03-8.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem