Category: 17417-09-3

17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 2-Fluoro-5-nitrobenzonitrile

Part A: Preparation of 2-fluoro-5-aminobenzonitrile. To a solution of 2-fluoro-5-nitrobenzonitrile(2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride(27.0 g, 120 mmol). The reaction-mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate(150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water(5×75 mL), brine(75 mL); dried over sodium sulfate(anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

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

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP946508; (2009); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application 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.

Part A Preparation of 2-fluoro-5-aminobenzonitrile To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5*75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

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; DuPont Pharmaceuticals Company; US6020357; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Product Details of 17417-09-3

Part A Preparation of 2-fluoro-5-aminobenzonitrile To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5*75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

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; DuPont Pharmaceuticals Company; US6020357; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 17417-09-3, 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. 17417-09-3 name is 2-Fluoro-5-nitrobenzonitrile, 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.

2-Morpholin-4-yl-5-nitro-benzonitrile 3-Cyano-4-fluoronitrobenzene (3.3 g, 19.9 mmol) was dissolved in ethyl acetate (10 mL). Morpholine (2.2 mL, 25 mmol), and N,N-diisopropylethylamine (3.5 mL, 20 mmol) were added and the mixture stirred overnight at room temperature. At 17 h, additional ethyl acetate (150 mL) was added and the combined mixture was washed with water (50 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was used without further purification.

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.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/87575; (2004); A1;; ; Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Quality Control of 2-Fluoro-5-nitrobenzonitrile

General procedure: General procedure: 3-Hydroxy oxetane (370 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0 C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0 C. Then 2-fluoro-5-nitrobenzonitrile (415 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0 C and allowed to warm up to ambient temperature over 1 hour. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (x2), dried over Na2S04, filtered, and concentrated to provide 5-nitro-2-(oxetan- 3-yloxy)benzonitrile (495 mg, 90%) as a brown-yellow solid that was used without further purification. [00576] 1H NMR (300 MHz; 6-DMSO) delta 8.74-8.75 (m, 1H), 8.42-8.47 (m, 1H), 7.09- 7.12 (dd, 1H, J = 0.9Hz, J = 9.3Hz), 5.56-5.63 (m, 1H), 4.96-5.00 (m, 2H), 4.59-4.63 (m, 2H); m/z = 221 (M+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 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 3-cyano-4-fluoronitrobenzene (0.530 g, 3.19 mmol) and N- (2-fluoro-5-hydroxyphenyl) -2- [3- (trifluoromethyl) phenyl] acetamide (1.00 g, 3.19 mmol) in N, N- dimethylformamide (5 mL) was added potassium carbonate (0.530 g, 3.83 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate (100 mL) , washed successively with water (100 mL) and saturated brine (100 mL) , and dried over anhydrous magnesium sulfate. Insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: 50% ethyl acetate/n-hexane) , and the obtained solution was concentrated under reduced pressure to give the title compound (1.38 g, 94%) as a yellow oil. 1H-NMR (DMSO-d6, 300 MHz) delta 3.91 (2H, s) , 7.01 (IH, d, J = 9.3 Hz), 7.08 – 7.16 (IH, m) , 7.48 (IH, dd, J = 10.7, 9.0 Hz), 7.52 – 7.66 (3H, m) , 7.70 (IH, s) , 7.98 (IH, dd, J = 6.6, 3.0 Hz), 8.39 – 8.44 (IH, m) , 8.84 (IH, d, J = 2.7 Hz), 10.31 (IH, s) .

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; OKANIWA, Masanori; TAKAGI, Terufumi; WO2010/64722; (2010); 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., category: nitriles-buliding-blocks

2-Fluoro-5-nitrobenzonitrile (50 g, 0.3 mol) was dissolved in 500 ml of dimethylsulfoxide and potassium carbonate (49.7 g,0.36 mol) and sodium methanesulfinate (36.7 g, 0.36 mol) was added.Heated to 100 C overnight reaction, TLC detection (EpsilonAlpha: PE =1: 1), the reaction is over.After the reaction solution was poured into 100 mL of water, no solid was precipitated, and extracted with EA (250 mL * 4). The combined EA phases and sulfuric acidSodium dried, concentrated by column chromatography to give a yellow brown solid (5g, yield 7.4%);Intermediate 5g suspended in 100mL of water, add10 mL of concentrated hydrochloric acid was added and the mixture was stirred for 30 minutes. TLC (EA: PE = 1: 1) was performed. The reaction was completed and the reaction mixture was extracted with DCMTake, merge DCM phase three times,Saturated brine (100mL * l), the organic phase was dried over sodium sulfate, concentrated to give a solid which was purified by column chromatography to give a yellow powder (3.00g, 7.3 ·)

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

Reference:
Patent; Qidong Shaoyuan Chemical Technology Co., Ltd.; Li Shaobo; Wu Yong; Gai Hongguang; Xie Chunhui; Guo Meng; (5 pag.)CN104744429; (2016); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 17417-09-3, The chemical industry reduces the impact on the environment during synthesis 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

Intermediate 82A: 2-(3-Ethyl-2-oxo-pyrrolidin-1-yl)-5-nitro-benzonitrile To a solution of 3-ethylpyrrolidin-2-one (0.89 g, 7.865 mmol) in DMF (25 mL) was added sodium hydride (60%, 346 mg, 8.651 mmol) at 0 C. (ice-bath). The mixture was stirred for 30 minutes at 0 C., then the ice-bath was removed and the mixture stirred for another 30 minutes at RT. A solution of 2-fluoro-5-nitrobenzonitrile (1.306 g, 7.865 mmol) in DMF (5 mL) was added dropwise via syringe and the resulting dark red solution was stirred for 1 hour at RT. The reaction mixture was poured into a mixture of 2M HCl (50 mL) and crushed ice (?50 g) and the organics were extracted with EtOAc (3*50 mL). The combined organic extracts were washed with water (80 mL) and brine (50 mL), dried (Na2SO4) and concentrated at reduced pressure. Purification by Biotage Isolera chromatography (silica gel, eluting with heptanes-EtOAc, 1:0 to 1:1) afforded the title compound (racemic mixture; 1.18 g, 57% yield) as pale yellow solid. 1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.74 (d, J=2.7 Hz, 1H), 8.54 (dd, J=9.0, 2.7 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 4.05-3.97 (m, 1H), 3.87-3.80 (m, 1H), 2.66-2.57 (m, 1H), 2.37-2.28 (m, 1H), 1.91-1.73 (m, 2H), 1.58-1.46 (m, 1H), 0.97 (t, J=7.5 Hz, 3H); LCMS (Analytical Method A): Rt=1.06 mins, MS (ESIpos): m/z=259.95 (M+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, 2-Fluoro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Baeurle, Stefan; Nagel, Jens; Rotgeri, Andrea; Davenport, Adam James; Stimson, Christopher Charles; (86 pag.)US2019/194148; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Recommanded Product: 17417-09-3

General procedure: To a partial solution of the diazeniumdiolate 3 or 14 (1 equiv) in DMSO (4 mL/mmol of diazeniumdiolate salt) was added the fluoro compound (4-8) (1 equiv) in THF (2 mL/mmol of fluoro compound) at room temperature. The resulting solution was stirred at room temperature overnight. To this homogeneous solution, water was added (8 mL/mmol of diazeniumdiolate), producing a yellow precipitate that was collected by filtration, washed with water, and dried. The crude product was purified by flash column chromatography or by recrystallization.

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:
Article; Nandurdikar, Rahul S.; MacIag, Anna E.; Holland, Ryan J.; Cao, Zhao; Shami, Paul J.; Anderson, Lucy M.; Keefer, Larry K.; Saavedra, Joseph E.; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3094 – 3099;,
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, Recommanded Product: 2-Fluoro-5-nitrobenzonitrile

2-(1-Pyrrolidinyl)ethanol (770 mul_, 12.0 mmol) was injected into a 00C stirred suspension of 2-fluoro-5-nitrobenzonitrile (1.0 g, 6.0 mmol), 60% w/w NaH as a suspension in oil (361 mg, 9.0 mmol) and DMF (10 ml_). The ice bath was removed and the reaction was allowed to warm to rt. TLC confirmed consumption of the starting material and the DMF was removed under vacuum. The resulting residue was partitioned between EtOAc and water. The organic fraction was washed with brine and dried over MgSO4. The organic fraction was concentrated and purified by silica gel chromatography (gradient: 0-100%(90%CH2Cl2:9%MeOH:1%NH4OH)/CH2Cl2). Purification provided 330 mg (22%) of 5-nitro-2-{[2-(1-pyrrolidinyl)ethyl]oxy}benzonitrile. 1H NMR (400 MHz, DMSO-c/6) delta ppm 8.62 – 8.69 (m, 1 H), 8.47 (ddd, J = 9.3, 2.9, 0.9 Hz, 1 H), 7.46 (d, J = 9.3 Hz, 1 H), 4.37 (t, J = 5.5 Hz, 2 H), 2.84 (t, J = 5.7 Hz, 2 H), 2.53 (s, 4 H), 1.65 (s, 4 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, 2-Fluoro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts