Author: Jessica.F

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. 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6N2O2

(b) Synthesis of 4-amino-2-methylbenzonitrile Tin chloride dihydrate (18.5 g, 82.0 mmol) was added to a solution of 2-methyl-4-nitrobenzonitrile (3.80 g, 23.4 mmol) in ethanol (140 ml), and the resulting mixture was stirred for 3 hours under refluxing conditions. After completion of the reaction, the solvent was distilled off and the resulting residue was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution. After the precipitate obtained during the washing was filtered by the use of Celite, the filtrate was extracted with ethyl acetate and the extract solution was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 4-amino-2-methylbenzonitrile (2.89 g, 94%).

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 89001-53-6.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 70591-86-5, These common heterocyclic compound, 70591-86-5, name is 3-Bromobenzoylacetonitrile, 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.

Example IV-34 3-(3-bromophenyl)-5-isoxazolamine To a solution of 3-(3-bromophenyl)-3-oxopropanenitrile (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (*1). The organic layer was washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification. LC/MS (method B) 2.21 min, m/z 239, 241 (Br isotopes).

The synthetic route of 70591-86-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); 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. 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Chloro-5-fluorobenzonitrile

Step 3: 3-Chloro-5-{[5-chloro-l-(4-methoxybenzyl)-lH-l,2,3-benzotriazol-4- yl]oxy}benzonitrile; A stirred suspension of 5 -chloro-l-(4-methoxybenzy I)- IH- 1,2, 3 -benzotriazol-4-ol (0.050 g, 0.173 mmol), 3-fluoro-5-chloro-benzonitrile (0.081 g, 0.518 mmol) and cesium carbonate (0.068 g, 0.207 mmol) in NMP (1.5 mL) was heated at 1400C for 72 hours. The reaction mixture was then quenched with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2 x 100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2theta, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2 x 100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to yield the title product. lH NMR (DMSO dbeta) delta 7.90- 7.88(m, IH), 7.80(s, IH), 7.79-7.75(m, IH), 7.60-7.55(m, 2H), 7.40-7.35(d, J-6.9Hz, 2H), 6.95- 6.88 (m, 2H), 5.80(s, 2H), 3.71(s, 3H).

According to the analysis of related databases, 327056-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/76223; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 51762-67-5, name is 3-Nitrophthalonitrile, 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 51762-67-5, Application In Synthesis of 3-Nitrophthalonitrile

General procedure: 2.60g (15.00mmol) 3-nitrophthalonitrile or 4-nitrophthalonitrile and 2.39g (15.50mmol) 2,6-dimethoxyphenol were dissolved in 30mL anhydrous dimethylsulfoxide (DMSO). After stirring for 15min, finely ground 5.39g (39mmol) anhydrous K2CO3 was added to this solution. The reaction mixture was stirred at 25C for 72h under nitrogen atmosphere. Then the mixture was poured into ice-water. The precipitated white product was filtered off, washed with water, and then dried in vacuum at 50C. The crude product was purified by column chromatography using silica gel eluting with chloroform (CHCl3).

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

Reference:
Article; Pi?kin, Mehmet; Polyhedron; vol. 104; (2016); p. 17 – 24;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

859855-53-1, name is 3-Amino-4-fluorobenzonitrile, 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. Recommanded Product: 3-Amino-4-fluorobenzonitrile

3-amino-4-fluorobenzonitrie (9.82 g, 72.1 mmol) was dissolved in acetonitrie to give a pale yellow solution. NBS (13.5g, 75.7 mmol) was added in portions; the reaction mixture tumed brown-blackish but remained a soution. After the completion of the reaction was confirmed by TLC and HPLC, silica gel was added to the reaction mixture and the solvent was evaporated under reduced pressure. The crude product was leaded on a CombiFlash column (330 g) and the product was eluted with hexanes/ethyl acetate (0 – 15% gradient). The clean fractions were combined to give 9.63 g (62%) of a yellowish off-white solid. More product was found in mixed fractions which were discarded. 1H NMR (300 MHz, dmso) 3 7.57 (d, J = 10.9 Hz. 1H). 7.17 (d. J= 8.7 Hz. 1H). 5.85 (s br. 2H); MS (ES) 213/215 (M-H).

The synthetic route of 859855-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; MCMURTRIE, Darren; KOLLURI, Rao; MASUDA, Esteban; TSO, Kin; ALVAREZ, Salvador; HECKRODT, Thilo; HOLLAND, Sacha; KELLEY, Ryan; DUNCTON, Matthew; SINGH, Rajinder; WO2014/89112; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 64248-62-0, 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. 64248-62-0 name is 3,4-Difluorobenzonitrile, 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.

3,4-difluorobenzonitrile (2.500 g, 17.973 mmol), titanium isoproxoxide (6.917 mL, 23.364 mmol) and ethylmagnesium bromide (1.00 M solution in THF, 41.337 mL, 41.337 mmol) was dissolved in 2-methoxy-2-methylpropane (MTBE, 30 mL), at -20 C and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture borontrifluoride diethyl etherate (4.436 mL, 35.945 mmol) was added and further stirring at room temperature for 3 hours, then, at room temperature, sodium hydroxide (3.00 M solution in water, 17.973 mL, 53.918 mmol) was added and the reaction was terminated by stirring for 30 minutes. The reaction mixture was filtered through a pad of celite to remove the solid. Water was poured into the filtrate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; methanol / dichloromethane = 5% to 30%) and concentrated to give the title compound (0.822 g, 27.0%) as a light yellow liquid.

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

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 873-74-5, 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. 873-74-5 name is 4-Aminobenzonitrile, 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.

The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-cyanoaniline, the reaction time is 12 h, and the other reaction and post-treatment processes are the same as in the embodiment 28. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

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

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Gao Xianying; Geng Yang; Han Shuaijun; Liang Apeng; Li Jingya; Zou Dapeng; Wu Yangjie; (19 pag.)CN108503552; (2018); A;,
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. 19179-31-8, name is 3,5-Dimethoxybenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO2

To a solution of 3,5-dimethoxybenzonitrile (2 g, 12.2 mmol) in dichloromethane (20 was added slowly BBr3 (15 mL, 1 M, 15 mmol) at -50 C under N2. After addition, the mixture was stirred at -50 C for 2 h and stirred at r.t for 20 hr. The mixture was slowly poured into ice-water with stirring and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column (petroleum ether/ethyl acetate (2: 1) as eluent) to afford 3,5- dihydroxybenzonitrile (1.43 g). 1H NMR (DMSO-d6, 400 MHz): delta 10.02 (s, 2H), 6.56 (d, J= 2.0 Hz, 2H), 6.51 (t, J = 2.0 Hz? 1H).

The synthetic route of 19179-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARRINGTON, Kenneth, L.; BURGEY, Christopher; GILFILLAN, Robert; HAN, Yongxin; PATEL, Mehul; LI, Chun Sing; LI, Yaozong; LUO, Yunfu; LEI, Zhiyu; XU, Jiayi; WO2014/58747; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 115279-73-7, A common heterocyclic compound, 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, molecular formula is C12H14N2, 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 500 ml four-necked flask equipped with a stirrer, a thermometer and a distillation system, 100 g of toluene and 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V) were added. 0.25 g of 4-dimethylaminopyridine, maintaining an internal temperature of 95-105 C. A solution of 12.9 g (0.05 mol) of ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV2) prepared in Example 4 and 30 g of toluene was added dropwise, and the mixture was dropped over 2 hours. Thereafter, the reaction was stirred at 110-115 C for 5 hours, and the formed ethanol was distilled off. After the reaction was completed, the temperature was lowered to 20-25 C, filtered, and the filter cake was washed with 20 g of toluene, the filtrate was combined, and toluene was distilled off under reduced pressure. The tert-butyl ether was recrystallized, filtered and dried to give 18.1 g of a white solid powder of eptatinib (I), yield 91.2%, liquid phase purity 99.92%, melting point 158.5-160.0 C.

The synthetic route of 115279-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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 78473-00-4, Recommanded Product: 78473-00-4

Into a 1000 mL three-neck flask were put 9.4 g (50 mmol) of 4-amino-3,5-dichlorobenzonitrile, 26 g (253 mmol) of isobutylboronic acid, 54 g (253 mmol) of tripotassium phosphate, 2.0 g (4.8 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 500 mL of toluene. The air in the flask was replaced with nitrogen, and this mixture was degassed while being stirred under reduced pressure. After the degassing, 0.88 g (0.96 mmol) of tris(dibenzylideneacetone)palladium(0) was added, and the mixture was stirred at 130 C. under a nitrogen stream for 8 hours to be reacted. Toluene was added to the reacted solution, and the solution was filtered through a filter aid in which Celite, aluminum oxide, and Celite were stacked in this order. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Toluene was used as a developing solvent. The resulting fraction was concentrated to give 10 g of a yellow oily substance in a yield of 87%. The obtained yellow oily substance was identified as 4-amino-3,5-diisobutylbenzonitrile by nuclear magnetic resonance (NMR) spectroscopy.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3,5-dichlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Seo, Satoshi; WATABE, Takeyoshi; MITSUMORI, Satomi; (178 pag.)US2017/92890; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts