Category: 17417-09-3

Application of 17417-09-3, A common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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.

To a solution of 2(H)-1,2,3-triazole (0.913 g, 13.24 mmol) in DMF (15 mL) was added portionwise sodium hydride (60% suspension in mineral oil, 0.530 g, 13.24 mmol) at rt and then stirred the mixture for 1H at room temperature. The reaction mixture was then cooled back down to OeC, and a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12.04 mmol) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 1.5 h at OeC and then at RT for 1.5 h. The mixture was quenched with ice cooled water and extracted with EtOAc (2/150 mL). The combined organic layers were washed with water (2/1,50 mL), brine (50 mL), dried (Na2SC>4) and filtered. The filtrate was rotary evaporated to leave a crude which was purified by flash column chromatography (silica gel, 20-30% EtOAc in hexanes as eluent) to give 5-nitro-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.2 g, 46.3% yield) & 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile (0.7 g, 27.0% yield). 5-nitro-2-(2H-1,2,3-triazol-2-yl)benzonitrile: 1HNMR (400 MHz, DMSO-d6) ||8.93 (d, J = 2.5 Hz, 1H), 8.68 (dd, J = 8.5, 2.5 Hz, 1H), 8.44 (s, 2H), 8.40 (d, J = 8.5 Hz, 1H). ESI-MS (m/z) 216.04 (MH)+. 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile: 1HNMR (400 MHz, DMSO-d6) ||9.05 (d, J = 2.5 Hz, 1H), 8.95 (d, J = 1.3 Hz, 1H), 8.75 (dd, J = 8.5, 2.5 Hz, 1H), 8.20 (d,J = 8.5 Hz, 1H), 8.15 (d, J = 1.3 Hz, 1H); ESI-MS (m/ z) 216.00 (MH)+.

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, belongs to nitriles-buliding-blocks 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 17417-09-3, Computed Properties of C7H3FN2O2

Under room temperature, into the 3-amino-4-fluorophenol (3 g, 22.42mmol) and 2-fluoro-5-nitrobenzonitrile (4.19 g, 24.66mmol) into DMF (20 mL) solution added K2CO3 (4.89g, 35.4mmol). The solution was stirred at 80C for 8h, and the solution was extracted with ethyl acetate, washed with saturated sodium chloride, drying with anhydrous sodium sulfate, filtering out insoluble matter, filter and concentrate under reduced pressure, the residue obtained was purified by silica gel column chromatography, (eluent: petroleum ether / ethyl acetate = 5:1 -4:1), and the resulting solution was concentrated under reduced pressure, obtained 1.95 g of a light yellow solid, yield is 35%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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. Product Details of 17417-09-3

6A: 2-(Ethylsulfonyl)-5-nitrobenzonitrile; [00219] Ethanethiol (2.8 mL, 38 mmol) was added to a solution of 2-fluoro-5- nitrobenzonitrile (5.00 g, 30.1 mmol) and triethylamine (9.3 mL, 67 mmol) in DMF (100 mL). The reaction mixture was stirred for 1 h and then poured into water (500 mL). The resulting precipitate was isolated by filtration, dissolved in DCM, washed with water and brine, dried (MgSO^, and concentrated under reduced pressure. The residue (6.14 g) was dissolved in DCM (100 mL), cooled to 0C, and treated with MCPBA (16.0 g, 71 mmol) in one portion. The reaction mixture was allowed to stir at rt overnight, and then was extracted with sodium bicarbonate solution (saturated), sodium bisulfite solution (10%), and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 6A (5.6 g, 80%) as a pale yellow solid. IH NMR (400 MHz, CDCl3) delta 1.02 (s, 6H), 1.97 (m, 2H), 2.36 (t, J = 7.5 Hz, 2H), 2.68 (t, J= 7.7 Hz, 2H), 3.76 (s, 4H), 7.18 (d, J= 7.9 Hz, 2H), 7.72 (d, J= 7.5 Hz, 2H).

The synthetic route of 2-Fluoro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-5-nitrobenzonitrile

A solution of 2-fluoro-5-nitro-bezonitrile (300 mg, 1.81 mmol) and methyl hydrazine (170 mg, 3.62 mmol) in dioxane (10 mL) was stirred at 80 C. for 2 h. The reaction mixture was cooled and partitioned between 1N aqueous HCl and EtOAc. The organic layer was washed with water dried over Na2SO4 filtered and concentrated to the desired product 5-nitro-1-methyl-1H-indazol-3-ylamine (280 mg, 80%). HRMS for C8H8N4O2 (M+H) calcd: 193.0720. Found:193.0720

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 of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), 1H-1,2,3-triazole (228.68 mg, 3.31 mmol) and potassium carbonate (832.02 mg, 6.02 mmol) were added to MeCN (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with EtOAc (30 mL*2). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid, which was purified by FCC (petroleum ether/ethyl acetate from 100:0 to 70:30) to afford the title compound (600 mg, 92.6%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) 6=8.72 (d, J=2.6 Hz, 1H), 8.55 (dd, J=2.4, 9.0 Hz, 1H), 8.42 (d, J=9.3 Hz, 1H), 8.03 (s, 2H).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 17417-09-3, 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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of benzonitrile 1 (10.0 mmol) and methylhydrazine (2.8 mL, 50.0 mmol) in EtOH (10.0 mL) was heated to reflux overnight. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using EtOAc/hexanes (1:1) as eluent to give the product 2.

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

Reference:
Article; Liu, Han-Jun; Hung, Shiang-Fu; Chen, Chuan-Lin; Lin, Mei-Huey; Tetrahedron; vol. 69; 19; (2013); p. 3907 – 3912;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

Step D. 2-[1-(2-Cyano-4-nitro-phenyl)-piperidin-4-yl]-N-ethyl-2-phenyl-acetamide. To a solution of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (500 mg, 2 mmol) and 2-fluoro-5-nitro-benzonitrile (337 mg, 2.03 mmol) in DMF was added K2CO3 (840 mg, 6.1 mmol). The solution was heated to 80 C. for 16 h. After cooling to rt, H2O and 3:1 EtOAc/hexanes were added. The organic portion was washed three times with H2O and once with brine, dried (Na2SO4) and concentrated to provide the title compound (yellow powder, 686 mg, 86%).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 17417-09-3, 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 17417-09-3 as follows.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), triazole (228.7 mg, 3.31 mmol) and K2CO3 (832.0 mg, 6.02 mmol) were added to THF (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with ethyl acetate (30 mL*3). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid. The crude solid was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile, 11a (500 mg, 77.2%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.74 (d, J=2.6 Hz, 1H), 8.65 (dd, J=2.4, 9.0 Hz, 1H), 8.48 (d, J=0.9 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 7.98 (d, J=0.9 Hz, 1H).

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

Step-1: 2-Fluoro-5-nitrobenzonitrile (1.4g, 1.0 eq, 8.4 mmol) was taken in annhydrous DMF (10 mL). Secondary amine (1.2 eq, 10.12 mmol) was added to the above solution followed by the addition of K2C03 (3.5g, 3.0eq, 25.3 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with EtOAc (100 mL) and partitioned with water (100 mL). Organic layers were separated and the aqueous layers were washed with EtOAc (1 x 50 mL). The combined oragnic layers were washed with aqueous staurated NaHC03 solution (100 mL) and dried over Na2S04. Organic layers were concentrated under reduced pressure to leave a crude mixture. The mixture was purified by column chromatography on silica gel (ISCO System) using EtOAc / Hexane (gradient system from 0: 1 to 2:8) as eluent to give the product as a solid. 2-(4-(Methylsulfonyl)piperazin-l-yl)-5-nitrobenzonitrile: Synthesized as described in Step-1. Yield = 73%, 1H NMR (300 MHz, CDC13) delta 8.43 (d, J = 2.1 Hz, 1H), 8.27 (dd, J = 9.3, 2.7 Hz, 1H), 6.98 (d, J = 9.3 Hz, 1H), 3.59 – 3.48 (m, 4H), 2.68 – 2.57 (m, 4H), 2.38 (s, 3H); LCMS (m z): 311 (M+H)+.

Statistics shows that 2-Fluoro-5-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17417-09-3.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, belongs to nitriles-buliding-blocks 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 17417-09-3, SDS of cas: 17417-09-3

To a solution of 2-fluoro-5-nitrobenzonitrile (5.0 g, 30 mmol) in DMF (50 mL) was added TEA (6.1 g, 60 mmol), and 4-phenoxyaniline (7.4 g, 30 mmol), the reaction was warmed to 110 C. for 16 h. After cooling down to RT, the reaction was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with water (20 mL¡Á2), dried over Na2SO4, filtered, concentrated and purified by column chromatography on silica gel (200-300 mesh, PE/EA=2/1) to give the product about 5.0 g (50.4%). MS (ESI) m/e [M+1]+332.1

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-Fluoro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wang, Zhiwei; Guo, Yunhang; US2015/5277; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts