Category: 317-20-4

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 317-20-4 as follows. 317-20-4

General procedure: To an aqueous mixture of 4-hydroxy-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 3a (2 mmol), aldehyde 5 (2 mmol), malononitrile 4 (2 mmol) and piperidine (10 mol %) were added successively at room temperature under an open atmosphere with vigorous stirring. The progress of the reaction was monitored by thin layer chromatography. The precipitated solid was ltered, washed with water (10 mL) and ethanol (5 mL) and then with ether (3 mL). The product was dried under vacuum.

According to the analysis of related databases, 317-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jayarajan, Ramasamy; Vasuki, Gnanasambandam; Tetrahedron Letters; vol. 53; 24; (2012); p. 3044 – 3048;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, Name is 7-Fluoroisatin, 317-20-4, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step 1: Preparation of 7-fluoro-1-methyl-1H-indole-2,3-dione 7-Fluoro-1H-indole-2,3-dione (prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325, 1.0 g, 6.05 mmol), iodomethane (1.13 ml, 18.2 mmol) and potassium carbonate (1.65 g, 12.1 mmol) in DMF (15 ml) are stirred at room temperature for 24 hours. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4), and evaporated to give the title compound as an orange solid. HPLC r.t. 3.79 min; MS for C9H1FNO2 m/z 180.0(M+H)+.

Statistics shows that 7-Fluoroisatin is playing an increasingly important role. we look forward to future research findings about 317-20-4.

Reference:
Patent; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 317-20-4 name is 7-Fluoroisatin, 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. 317-20-4

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroisatin, and friends who are interested can also refer to it.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 317-20-4, name is 7-Fluoroisatin, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 317-20-4

General procedure: The mixture of substituted isatins 1 (1 mmol), phthalic anhydride or succinic anhydride 2 (1 mmol), 1,3-dimethylurea (1,3-diethylurea) 3 (1.5 mmol), p-TSA?H2O (0.2 mmol), and CH3CN (3 mL) was put in a 25 mL flask and reacted under 80 C (monitored by TLC) about 5 h. After completion, the reaction the mixture was cooled to room temperature and the precipitate was obtained by filtration. Compound 4 was purified by recrystallization from EtOH.

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, 317-20-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Lei; Xu, Hui; Yan, Lirong; Xu, Zhongyun; Ling, Zhi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron Letters; vol. 58; 25; (2017); p. 2468 – 2474;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, 317-20-4

In a 25 ml round bottom flask were added N, N’-dibutyl-2-nitroethylene-1,1-diamine (1 mmol) and 7-Indoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mmol) were added under heating with magnetic stirringTo 110 C for 14 hours. The reaction was monitored by TLC, until the point of complete disappearance of raw materials, the reaction was added 50 ml of acetic acidEster and 50 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous Na 2 SO 4. The dried organicThe phase was concentrated to dryness decompression pressure, after adding 3 ml of concentrated dry distillate acetone and 4 grams of 100 ~ 200 mesh silica gel Stirred byDrying under pressure, loading the sample, separating and drying on a silica gel column using a petroleum ether / ethyl acetate = 7: 1 eluent to obtain a red solid product N-butyl-2- (Butylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (Compound 32) in 90% 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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, A common compound: 317-20-4, name is 7-Fluoroisatin, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

N,N-dimethylformamide (540.0 mL, 6980 mmol, 100 mass%) was added to a 2-L ChemGlass reactor equipped with a mechanical agitator, a temperature probe, and a cooling/heating circulator. Next, 7-fluoroindoline-2,3-dione (135.0 g, 817.6 mmol, 100 mass%) was added at 25 C and dissolved to form a dark red solution. The charging ports and the beaker that contained the 7-fluoroindoline-2,3-dione were washed with N,N-dimethylformamide (135.0 mL, 1750 mmol, 100 mass%) and the rinse solution was poured into the reactor. Next, cesium carbonate 60-80 mesh (203.66 g, 625.05 mmol, 100 mass%) was added portion-wise to the reaction mixture. The addition was exothermic and the temperature of the reaction mixture increased from 20 to 25.5 C. The color of the reaction mixture changed from a dark red solution to a black solution. The reactor jacket temperature was set to 0 C. Next, iodomethane (56.5 mL, 907 mmol, 100 mass%) was added slowly via an additional funnel at ambient temperature, (iodomethane temperature) while maintaining the batch temperature at less than 30 C. Upon stirring, the reaction was exothermic, reaching a temperature of 29.3 C. The batch temperature decreased to 26.3 C after 85% of iodomethane was added, and the reaction mixture turned from black to an orange. After the addition of the iodomethane was completed, the jacket temperature was raised to 25.5 C. The reaction mixture was stirred at 25 C for 2 hrs. The reddish orange-colored reaction mixture was transferred to a 1 L Erlenmeyer flask. The reaction mixture was filtered through a ceramic Buchner funnel with a No.1 Whatman filter paper to remove solid CS2CO3 and other solid by-products. In addition to a light-colored powder, there were yellow to brown colored rod-shaped crystals on top of the cake, which were water soluble. The filtrate was collected in a 2-L Erlenmeyer flask. The solids cake was washed with N,N-dimethylformamide (100.0 mL, 1290 mmol, 100 mass%). The DMF filtrate was collected in a 2-L Erlenmeyer flask. To a separate 5-L ChemGlass reactor was charged water (3000.0 mL, 166530 mmol, 100 mass%). Next, 1.66 g of 7-fluoro-l-methylindoline-2,3-dione was added as seed to the water to form an orange colored suspension. The DMF filtrate was charged to the 5-L reactor slowly while maintaining the batch temp, at less than 29 C over a period of 60 min. Stirring was maintained at 290 rpm. The orange solids precipitated instantly. The 2-L Erlenmeyer flask was rinsed with N,N-dimethylformamide (55.0 mL, 711 mmol, 100 mass%) and charged to the 5-L reactor. The slurry was cooled to 25 C and agitated at 200 rpm for 12 hrs. The mixture remained as a bright orange-colored suspension. The slurry was filtered over a No. l Whatman filter paper in a 9 cm diameter ceramic Buchner funnel to a 4L Erlenmeyer flask to provide a bright orange-colored cake. The cake was washed with 1200 mL of water via rinsing the 5000 mL reactor (400 mL x 2), followed by 300 mL of deionized water introduced directly on the orange cake. The wet cake was dried under suction for 40 min at ambient temperature until liquid was not observed to be dripping from the cake. The cake was introduced into a vacuum oven (800 mbar) with nitrogen sweeping at ambient temperature for 1 hr, at 40-45 C for overnight, and at 25 C for 1 day to provide 7-fluoro-l-methylindoline-2,3-dione (Q, 130.02 g, 725.76 mmol, 100 mass%, 88.77% yield) as a bright orange-colored solid. NMR (400 MHz, DMSO- de) delta 7.57 (ddd, J=12.0, 8.5, 1.0 Hz, 1H), 7.40 (dd, J=7.3, 1.0 Hz, 1H), 7.12 (ddd, J=8.5, 7.5, 4.0 Hz, 1H), 3.29 (d, J=3.0 Hz, 3H). 13C NMR (101 MHz, DMSO-de) delta 182.3, 158.2, 148.8, 146.4, 137.2, 125.9, 124.3, 120.6, 28.7.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARRASQUILLO, Ronald; GENG, Peng; HUANG, Eric C.; KATIPALLY, Kishta; LEE, Andrew; MUDRYK, Boguslaw; QIAN, Xinhua; RAZLER, Thomas M.; WANG, Jianji; WEI, Carolyn S.; WISNIEWSKI, Steven R.; ZHU, Ye; (79 pag.)WO2018/118830; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life.

Step 1a: Preparation of 7-fluoro-1-methyl-1H-indole-2,3-dione (6) 7-Fluoro-1H-indole-2,3-dione (5, prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325, 3.00 g, 0.182 mol), iodomethane (3.40 ml, 0.545 mol) and potassium carbonate (4.92 g, 0.0363 mol) in DMF (15 ml) are stirred at room temperature for 1 hour. The reaction mixture is diluted with cold water and the resulting precipitate filtered and dried to give the title compound as a solid. HPLC r.t. 4.01 min; MS for C9H6FNO2 m/z 180.0 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 7-Fluoroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. 317-20-4

Add in a 25 mL round bottom flask(E) -N-4-chlorobenzyl) -N- (4-methylbenzyl) -2-nitroethylene-1,1-diamine(1 mmol)And 7-fluoroindoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mlMole) was heated under magnetic stirring to 110 C for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solutionThe mixture was extracted with 50 ml of ethyl acetate and 50 ml of saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfateDry, with petroleum ether / ethyl acetate = 7: 1 eluent silica gel column was dried to give a yellow solidThe product N- (4-chlorobenzyl) -2-(4-chlorobenzylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (compound 30) in 75% yield.

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 317-20-4.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

0.4 mmol of 7-fluoroisatin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under an oil bath of 80 C for 29 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-10 (light yellow solid, yield 84%, purity 99.8%) was obtained.

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; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem