Category: 50397-74-5

Synthetic Route of 50397-74-5, These common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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.

In another example of a dye compound according to Formula 1, the dye compound has the following formula: This compound is (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide may be synthesised as follows: A suspension of 4-Amino-3-bromobenzonitrile (15.0 g, 76.1 mmol) in a mixture of AcOH (120 mL) and EtCO2H (80 mL) was warmed until a clear solution was obtained and then cooled to 8 C. with an ice bath. 40% nitrosyl sulfuric acid (14.3 mL, 83.7 mmol) was added drop wise. The mixture was stirred 1 h at 7 C. and then added slowly to a solution of N-{3-[bis(2-ethylhexyl)amino]-4-ethoxyphenyl}-2-ethylhexanamide (35.0 g, 69.6 mmol) in 1,4-dioxane (120 mL) and acetic acid (30 mL) cooled in an ice bath. The mixture was stirred at 7 C. during 1 h and then hydrolyzed by drop wise addition of 33% NaOH (75 mL) while cooling in an ice bath. After 30 minutes, the mixture was poured into water and extracted with toluene. The combined organic layers were washed with water and the solvent evaporated. Purification by column chromatography (silicagel, heptane/EtOAc 60/1) afforded (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2-bromo-4-cyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (35 g). This was dissolved in dimethylformamide DMF (400 mL) and copper(I) cyanide (17.6 g, 196.9 mmol) was added while the mixture was cooled in a water bath. After 20 h of stirring at RT, the reaction mixture was poured into 15% ammonia and extracted with toluene (3*). The combined organic layers were washed with ammonia, water and dried with Na2SO4. After evaporation of the solvent the residue was purified by column chromatography (silicagel, heptane/EtOAc 80/1 to 30/1) to obtain (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (19.8 g, 39% yield) as a purple oil.

Statistics shows that 4-Amino-3-bromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 50397-74-5.

Reference:
Patent; Amazon Technologies, Inc.; Leguijt, Robin; Mans, Jurrinn; Sandhu, Sukhdip; US2015/370062; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 50397-74-5, 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 50397-74-5 as follows.

General procedure: Aniline 1 (0.5 mmol), H2O (5 mL), KOH (1 mmol, 2 equiv), and the CTAB (0.05 mmol, 10% mmol) were added to the reaction vessel stirring for 5 min. Allyl bromide (1 mmol, 2 equiv) was added, while maintaining the temperature at 80 C for 10 min under microwave irradiation (850 W). After completion of the reaction, the mixture was extracted with CH2Cl2 (3 × 15 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, and evaporated. The residue was purified by column chromatography (petroleum ether/ethyl acetate) to afford N-allylaniline 2a-j.

According to the analysis of related databases, 50397-74-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meiyu; Wang, Xie; Sun, Xiaoliang; He, Wei; Tetrahedron Letters; vol. 55; 16; (2014); p. 2711 – 2714;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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 50397-74-5, Computed Properties of C7H5BrN2

To a mixture of 4-amino-3-bromobenzonitrile (10.0 g, 0.050 mmol) and methyl acrylate (9.19mL, 0.101 mmol) in acetonitrile (200 mL) was added palladium acetate (0.568 g, 0.0025mmol) and tri-o-tolyl phosphine (1.54 g, 0.005 mmol) and Et3N (14.64 mL, 0.105 mmol). The reaction mixture was heated to reflux for 48 h. The reaction mass was filteredthrough celite and washed the bed with ethyl acetate. The filtrate was concentrated to afford 6.0 g of title product. ?H NMR (300 MHz, DMSO-d6): 7.92 (s, 1H), 7.82-7.77 (d, J = 15.6Hz, 1H), 7.4 1-7.38 (d, J = 8.7 Hz, 1H), 6.77-6.74(d, J = 8.7 Hz, 1H), 6.64 (s, 2H), 6.56-6.5 1 (d, J= 15.6 Hz, 1H), 3.70 (s, 3H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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. COA of Formula: C7H5BrN2

4 – Amino -3 – bromoxynil (4 – Amino – 3 – bromobenzonitrile) 50.0g (253.76 mmol), 4 – bromobenzoyl chloride (4 – Bromobenzoyl chloride) 55.7g (253.76 mmol) 500 ml and pyridine (Pyridine) 12 hoursAfter completion of the reaction, the solvent was distilled under reduced pressure. A slightly yellow solid compound (intermediate (5)) 75.6g (=unitz ) was obtained using diisopropyl ether (IPE) to carry out the solid-state reaction with diisopropyl ether (IPE 78.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50397-74-5, its application will become more common.

Reference:
Patent; Co., Ltd. Leputuo; Wu Weizhen; Han Jiazhong; Jin Huizhen; Jin Xiane; Jin Kuili; Ren Zhezhu; Xi Wenji; Gao Bingzhu; (46 pag.)CN109988119; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 50397-74-5,Some common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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 compound 54-1 (1 g, 5.08 mmol, 1 eq.) in DMF (7 mL) and TEA (2.18 g, 21.55 mmol, 3 mL, 4.25 eq.) was added compound 54-2 (683.15 mg, 6.09 mmol, 783.43 uL, 1.2 eq.),(48.33 mg, 253.77 umol, 0.05 eq.) and Pd(PPh3)2C12 (178.12 mg, 253.77 umol, 0.05 eq.). The mixture was stirred at 90 C under nitrogen atmosphere for 3 hours. TLC showed a new one spot formed. The reaction mixture was diluted with water (20 mL), extracted with EtOAc (20 mLx2),washed with brine (20 mL), dried with sodium sulfate, filtered and concentrated. The residue waspurified by flash silica gel column chromatography (PE:EA = 5:1) to give compound 3 (1 g, yield:86%) as a yellow oil. ?H NMR (400MHz, CDC13) 3 = 7.52 (d, J 1.6 Hz, 1 H), 7.34 (dd, J 8.6, 1.8Hz, 1 H), 6.68 (d, J= 8.4 Hz, 1 H), 4.76 (s, 2 H), 2.95 (s, 1 H), 2.88 (s, 1 H), 2.32 (s, 1 H), 1.85 -1.70 (m,4H), 1.10 (t,J7.4Hz,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-3-bromobenzonitrile, its application will become more common.

Reference:
Patent; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 50397-74-5, These common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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.

In another example of a dye compound according to Formula 1, the dye compound has the following formula: This compound is (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide may be synthesised as follows: A suspension of 4-Amino-3-bromobenzonitrile (15.0 g, 76.1 mmol) in a mixture of AcOH (120 mL) and EtCO2H (80 mL) was warmed until a clear solution was obtained and then cooled to 8 C. with an ice bath. 40% nitrosyl sulfuric acid (14.3 mL, 83.7 mmol) was added drop wise. The mixture was stirred 1 h at 7 C. and then added slowly to a solution of N-{3-[bis(2-ethylhexyl)amino]-4-ethoxyphenyl}-2-ethylhexanamide (35.0 g, 69.6 mmol) in 1,4-dioxane (120 mL) and acetic acid (30 mL) cooled in an ice bath. The mixture was stirred at 7 C. during 1 h and then hydrolyzed by drop wise addition of 33% NaOH (75 mL) while cooling in an ice bath. After 30 minutes, the mixture was poured into water and extracted with toluene. The combined organic layers were washed with water and the solvent evaporated. Purification by column chromatography (silicagel, heptane/EtOAc 60/1) afforded (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2-bromo-4-cyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (35 g). This was dissolved in dimethylformamide DMF (400 mL) and copper(I) cyanide (17.6 g, 196.9 mmol) was added while the mixture was cooled in a water bath. After 20 h of stirring at RT, the reaction mixture was poured into 15% ammonia and extracted with toluene (3*). The combined organic layers were washed with ammonia, water and dried with Na2SO4. After evaporation of the solvent the residue was purified by column chromatography (silicagel, heptane/EtOAc 80/1 to 30/1) to obtain (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (19.8 g, 39% yield) as a purple oil.

Statistics shows that 4-Amino-3-bromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 50397-74-5.

Reference:
Patent; Amazon Technologies, Inc.; Leguijt, Robin; Mans, Jurrinn; Sandhu, Sukhdip; US2015/370062; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 50397-74-5, 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 50397-74-5 as follows.

General procedure: Aniline 1 (0.5 mmol), H2O (5 mL), KOH (1 mmol, 2 equiv), and the CTAB (0.05 mmol, 10% mmol) were added to the reaction vessel stirring for 5 min. Allyl bromide (1 mmol, 2 equiv) was added, while maintaining the temperature at 80 C for 10 min under microwave irradiation (850 W). After completion of the reaction, the mixture was extracted with CH2Cl2 (3 × 15 mL). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, and evaporated. The residue was purified by column chromatography (petroleum ether/ethyl acetate) to afford N-allylaniline 2a-j.

According to the analysis of related databases, 50397-74-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meiyu; Wang, Xie; Sun, Xiaoliang; He, Wei; Tetrahedron Letters; vol. 55; 16; (2014); p. 2711 – 2714;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 50397-74-5, 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. 50397-74-5 name is 4-Amino-3-bromobenzonitrile, 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.

An ethanolic solution (5 mL) of 4-amino-3-bromobenzonitrile (L3, 1 mmol, 0.197 g) was added to ethanolicsolution (5 mL) of AgNO3 (0.6 mmol, 0.1 g). The test tube was covered with a perforated foil. Afterkeeping the solution in air for 4 days, light yellow crystals of 3 suitable for structure determinationwere obtained. Yield 80%, m.p. 130-132 C. Anal. Calcd for C21H15AgBr3N7O3: C, 33.15; H, 1.99; N, 12.88%. Found: C, 33.14; H, 1.97; N, 12.89%. IR (KBr, cm-1): 3481 (m), 3360 (s), 3215 (w), 2628 (w), 2221 (s), 1769(w), 1633 (s), 1594 (m), 1507 (s), 1388 (s). 1H NMR (400 MHz, DMSO) delta/ppm: 7.83 (d, J = 1.9 Hz, 1H), 7.45(dd, J = 8.5, 1.9 Hz, 1H), 6.82 (d, J = 8.5 Hz, 1H), 6.37 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-bromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Qian, Wei; Yuan, Hao-Kun; Zhang, Ran; Fang, Rui-Qin; Journal of Coordination Chemistry; vol. 69; 23; (2016); p. 3593 – 3602;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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: 4-Amino-3-bromobenzonitrile

50.0 g (253.76 mmol) of 4-amino-3-bromobenzonitrile, 4-bromobenzoyl chloride 55.7 g (253.76 mmol) of (4-bromobenzoyl chloride) and 500 mL of pyridine were added thereto, followed by stirring at reflux for at least 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. Solid to pale yellow by solidification with diisopropyl ether (IPE) 75.6 g (yield: 78.3%) of a mixture (intermediate (12)) was obtained.

The synthetic route of 50397-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Raepto Co., Ltd.; Seok Mun-gi; Go Byeong-su; Im Cheol-su; Kim Hyeon-a; Kim Gyu-sik; Park Yong-pil; Han Gap-jong; Oh Yu-jin; (37 pag.)KR102059550; (2019); B1;,
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. 50397-74-5, name is 4-Amino-3-bromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5BrN2

Remarkably, the unprotected amine function in 4-amino-3-bromobenzonitrile (5c) is well tolerated in the one-pot coupling procedure and the biphenyl 6d was isolated in 79 % 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 50397-74-5.