Category: 324-03-8

Quality Control of 6-Fluoroindoline-2,3-dione, Having gained chemical understanding at molecular level, chemistry graduates may choose to apply this knowledge in almost unlimited ways, as it can be used to analyze all matter and therefore our entire environment.

To a stirred solution of starting material E-1.1-6 (55.0 g; 333.1 mmol) in DMF (550 ml_) is added K2CO3 (55.2 g; 399.7 mmol) and 2-iodo-propane (73.6 g; 433.0 mmol) at 25 C. The reaction mixture is stirred at 25 C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer is concentrated under reduced pressure to obtain crude compound. The crude is purified by column chromatography using silicagel (230-400 pm) with eluting mixture of ethyl acetate and hexane. Yield: 51 % (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method RND-FA-4.5-MIN

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Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
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Chemical research careers are more diverse than they might first appear, as there are many different reasons to conduct research and many possible environments. Computed Properties of C8H4FNO2

To a mixture of 5.0 g (30.3 mmol) 6-fluoro-1H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid,which was used without further purification. Yield: 6.02 g (85%).1H-NMR (300 MHz, DMSO d6) 6 (ppm) = 7.78 (ddd, 1H), 7.99 (dd, 1H), 8.42 (s, 1H),8.89 (dd, 1H).

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Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; BUCHMANN, Bernd; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; KOPITZ, Charlotte Christine; (285 pag.)WO2016/202935; (2016); A1;,
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While the job of a research scientist varies, most chemistry careers in research are based in laboratories, where research is conducted by teams following scientific methods and standards. , Formula: C8H4FNO2

Add 11.33g NaNO3 and 100mL H2SO4 to a 500mL reaction flask.With stirring, the temperature of the ice bath was lowered to 0 C. Take 20.00g of compound 1-1,Dissolved in 120mL H2SO4,Slowly add the 1-1 H2SO4 solution to the reaction flask,After dripping, the reaction was held at 0 C for 1 hour, and then the reaction solution was poured into 1 L of ice water.After stirring for 0.5 hours, it was filtered and the filter cake was washed with water until neutral.The filter cake was washed with 80 mL of EtOH / H2O (7: 3) for 0.5 hours, filtered,The filter cake was dried to obtain 18.83 g of a crude product of 2-1.Yield: 74%.

As always, wish you can browse a selection of our May HOT articles below about 6-Fluoroindoline-2,3-dione.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Ma Dawei; Wang Kailiang; Xia Shanghua; Li Zheng; Zhao Jinlong; Li Ying; (82 pag.)CN110642874; (2020); A;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, Safety of 6-Fluoroindoline-2,3-dione

To a mixture of 5.0 g (30.3 mmol) 6-fluoro-1H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid,which was used without further purification. Yield: 6.02 g (85%).1H-NMR (300 MHz, DMSO d6) 6 (ppm) = 7.78 (ddd, 1H), 7.99 (dd, 1H), 8.42 (s, 1H),8.89 (dd, 1H).

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Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; BUCHMANN, Bernd; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; KOPITZ, Charlotte Christine; (285 pag.)WO2016/202935; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, Product Details of 324-03-8

6-Fluoro-l-isopropyl-lH-indole-2,3-dione E-1.2′”” To a stirred solution of 6-Fluoro-lH-indole-2,3-dione E-1.2″”” (55.0 g; 333.1 mmol) in DMF (550 ml) is added K2C03 (55.2 g; 399.7 mmol) and 2-Iodo- propane (73.6 g; 433.0 mmol) at 25C. The reaction mixture is stirred at 25C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain crude compound. The crude was purified by column chromatography using silicagel (230-400 muMu) with eluting mixture of ethyl acetate and hexane. Yield: 51% (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method R D-FA-4.5-MIN

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, SDS of cas: 324-03-8

Weigh rapamycin (0.05mmol), isatin 3g (0.10mmol) and rhodium octanoate (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 evaporation to give a crude product. The rapamycin analog I-g was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 88%.

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-Fluoroindoline-2,3-dione, 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;,
Indoline – Wikipedia,
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Reference of 324-03-8, These common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-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.

compound 119 6-fluoroindoline-2,3-dione (15.05 g, 91.1mmol), urea (5.47g, 91.1mmol), p-TSA (7.85 g, 45.57 mmol) and methyl acetoacetate (10.6 g, 91.1 mmol) in acetonitrile (500 mL) was refluxed overweekend. The reaction mixture was allowed to cool to room temperature. The precipitate was filtered off. The precipitate was taken up in CH2CI2 (1L) and saturated NaHC03 solution (500mL). The mixture was stirred vigorously during 15 minutes. The precipitate was filtered off and dried in vacuo, resulting in compound 119 as a beige powder (9.25 g). Method A; Rt: 0.61 m/z : 323.1 (M+NH4)+ Exact mass: 305.1; 1H NMR (400 MHz, DMSO-dg) delta ppm 2.24 (s, 3 H), 3.32 (s, 3 H), 6.57 (dd, J=9.4, 2.3 Hz, 1 H), 6.63 – 6.75 (m, 1 H), 7.13 (dd, J=8.0, 5.6 Hz, 1 H), 7.81 (s, 1 H), 8.31 – 11.56 (m, 2 H).

Statistics shows that 6-Fluoroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 324-03-8.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2013/102655; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, Formula: C8H4FNO2

7.96 g of the crude product of 6-fluoroisatin were added to 55 mE of water followed by the addition of 16.2 g (6 equivalents) of KOR while cooling with ice and stirring for 30 minutes. 9.9 g (1.5 equivalents) of bromoacetophenone were dropped into the resultant suspension while holding the internal temperature of the reaction mixture at 20 C. to 25 C. followed by additionally stirring overnight at room temperature. Afier neutralizing with concentrated hydrochloric acid, the precipitated crystals were filtered out and washed with a small amount of water. Afier adequately drying the resulting crystals, 7OmE of nitrobenzene heated to 120C. to 130C. were added a little at a time followed by further stirring for 1 hour at 140 C. to 150 C. After cooling the reaction mixture to room temperature, the precipitated crystals were washed with chloroform to obtain 5.4 g of 7-fluoro-3-hydroxy-2- methylquinoline.

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Reference:
Patent; Nippon Soda Co., Ltd.; Shibayama, Kotaro; Kuwahara, Raito; Sato, Motoaki; Nishimura, Satoshi; Shiinoki, Yasuyuki; Yokoyama, Masahiro; Kitamura, Juri; US2014/73792; (2014); A1;,
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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

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, category: indolines-derivatives

To a stirred solution of starting material E-1.1-6 (55.0 g; 333.1 mmol) in DMF (550 ml_) is added K2CO3 (55.2 g; 399.7 mmol) and 2-iodo-propane (73.6 g; 433.0 mmol) at 25 C. The reaction mixture is stirred at 25 C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer is concentrated under reduced pressure to obtain crude compound. The crude is purified by column chromatography using silicagel (230-400 pm) with eluting mixture of ethyl acetate and hexane. Yield: 51 % (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method RND-FA-4.5-MIN

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:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem