Category: 115661-37-5

Electric Literature of 115661-37-5, A common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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-amino-3-fluorobenzonitrile (17.07 g, 0.125 mol) in 1,4-dioxane (20 ml) was added 48% aqueous hydrobromic acid (200 ml) and the solution was cooled to 0C before adding dropwise a solution of sodium nitrite (9.95 g, 0.144 mol) in water (22 ml) over 35 min so that the temperature did not rise above 3C. The resulting mixture was stirred at 2-3C for 2 h then poured onto a cooled (5C) solution of copper (I) bromide (26.98 g, 0.188 mol) in 48% hydrobromic acid (100 ml). The mixture was stirred for 10 min then heated to 50C over 1 h. The mixture was cooled to ambient temperature, diluted with water (11) and extracted with diethyl ether (2 x 500 ml). The combined organic extracts were washed with 1 M aqueous Na2SO3 (500 ml), then saturated aqueous NH4C1 (200 ml), dried (MgSO4), and evaporated to give a brown oil/solid. Purification by chromatography (silica gel, 10% EtOAc/isohexane) and trituration of a mixed fraction with isohexane afforded 13.22 g (53%) of 2-bromo-3- fluorobenzonitrile as a pale yellow solid : 1H NMR (360 MHz, CDCl3) 5 7.62-7. 68 (1H, m), 7.74-7. 85 (1H, ddd, J 9, 9,1), 7.74-7. 85 (1H, ddd, J 8, 1, 1).

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:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93272; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, 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 115661-37-5, Recommanded Product: 2-Amino-3-fluorobenzonitrile

2-Amino-3-fluorobenzonitrile 45a (1 g, 7.35 mmol, purchased from Shanghai Bide Pharmatech Ltd.) was dissolved in 50 mL of dichloromethane. The reaction solution was added with N-bromosuccinimide (1.37 g, 7.71 mmol), and stirred for 16 hours. The reaction solution was added with water, and extracted with dichloromethane (50 mL×3). The organic phases were combined, washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 45b (1.25 g), yield: 79.13%. MS m/z (ESI):215.0 [M+1].

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Reference:
Patent; Jiangsu Hengrui Medicine Co. Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; LU, Biao; ZHANG, Junzhen; JIN, Fangfang; HE, Feng; TAO, Weikang; EP3569596; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 115661-37-5, A common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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-amino-3-fluorobenzonitrile (17.07 g, 0.125 mol) in 1,4-dioxane (20 ml) was added 48% aqueous hydrobromic acid (200 ml) and the solution was cooled to 0C before adding dropwise a solution of sodium nitrite (9.95 g, 0.144 mol) in water (22 ml) over 35 min so that the temperature did not rise above 3C. The resulting mixture was stirred at 2-3C for 2 h then poured onto a cooled (5C) solution of copper (I) bromide (26.98 g, 0.188 mol) in 48% hydrobromic acid (100 ml). The mixture was stirred for 10 min then heated to 50C over 1 h. The mixture was cooled to ambient temperature, diluted with water (11) and extracted with diethyl ether (2 x 500 ml). The combined organic extracts were washed with 1 M aqueous Na2SO3 (500 ml), then saturated aqueous NH4C1 (200 ml), dried (MgSO4), and evaporated to give a brown oil/solid. Purification by chromatography (silica gel, 10% EtOAc/isohexane) and trituration of a mixed fraction with isohexane afforded 13.22 g (53%) of 2-bromo-3- fluorobenzonitrile as a pale yellow solid : 1H NMR (360 MHz, CDCl3) 5 7.62-7. 68 (1H, m), 7.74-7. 85 (1H, ddd, J 9, 9,1), 7.74-7. 85 (1H, ddd, J 8, 1, 1).

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:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93272; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 115661-37-5, name is 2-Amino-3-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 115661-37-5

To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) over 10 min at 0C. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, 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 115661-37-5, Recommanded Product: 2-Amino-3-fluorobenzonitrile

2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile2-Amino-3-fluorobenzonitrile (1.1 g, 8.08 mmol) and 1-cyclopropyl-4-methoxy-1H-pyrrol-2(5H)-one (1.170 g, 7.64 mmol) were combined in acetic acid (10 mL) and heated to 80 C. Methanesulfonic acid (1.311 mL, 20.20 mmol) was dissolved in acetic acid (2 mL) and added dropwise via syringe over 15 minutes. The reaction was stirred for 1 hour at 80 C. and then cooled to RT and placed on a rotoevaporator under high vacuum for 15 minutes at 55 C. to remove the acetic acid. The resulting oil was dissolved in methylene chloride (80 mL) and slowly added dropwise over 20 minutes to a solution of saturated aqueous sodium bicarbonate (70 mL) mixed with 5 N sodium hydroxide (20 mL). This resultant biphasic system was separated. The aqueous was extracted 2 more times with methylene chloride (60 ml) and all organics were combined, dried over magnesium sulfate, and filtered. The filtrate was evacuated to produce 1.5 grams of tan solid. This solid was dissolved in methylene chloride and methanol. Silica gel was added (10 g) and solvent removed. The residue was purified via flash column eluting with ethyl acetate/methylene chloride to afford 2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile as an off white solid (87%). 1H NMR (500.333 MHz, DMSO) delta 9.18 (s, 1H), 7.70 (m,1H), 7.45 (m, 1H), 4.49 (s, 1H), 3.99 (s, 2H), 2.57 (m, 1H), 0.65 (m, 4H). MS APCI, m/z=258 (M+H). HPLC 1.66 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; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115661-37-5, The chemical industry reduces the impact on the environment during synthesis 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2-Amino-3-fluorobenzonitrile (9.8 g, 71.9 mmol) was bromo-deaminated as described in Example 1 to afford 2-bromo-3-fluorobenzonitrile as a pale brown solid: 1H NMR (360 MHz, CDCl3) delta 7.62-7.68 (1H, m), 7.74-7.85 (1H, ddd, J 9, 9, 1 Hz), 7.74-7.85 (1H, ddd, J 8, 1, 1 Hz).

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-Amino-3-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Carling, William Robert; Hallett, David James; Russell, Michael Geoffrey Neil; Street, Leslie Joseph; US2003/55060; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115661-37-5, A common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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 100 mL of the round bottom flask was added 1 g (about 7.35 mmol) of 2-amino-3-fluorobenzonitrile, 4.88 mL (about 36.73 mmol) of N,N-dimethylformamide dimethyl acetal and 15 mL of solvent methanol. The reaction in the round bottom flask was then stirred under reflux for 6 hours. The solvent and excess reactants are removed by distillation under reduced pressure. Intermediate (E)-N’-(2-cyano-6-fluorophenyl)-N,N-dimethylformamidine 1.4 g is obtained. The yield is 99%,

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Zhang Danqing; (31 pag.)CN110078675; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 115661-37-5,Some common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

A) N-(2-cyano-6-fluorophenyl)-3-oxobutanamide (0714) To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) at 0C over 10 min. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were sequentially added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts