Category: nitriles-buliding-blocks

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. 64248-64-2, name is 2,5-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 64248-64-2

EXAMPLE 23 (7RS,9aSR)-7-(4-Fluorophenoxy)methyl-2-(2-cyano-4-fluorophenyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine STR38 A mixture of 1.05 g (6.17 mmol) of (7RS,9aSR)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (U.S. Pat. No. 5,326,874) and 1.29 g (9.25 mmol) of 2,5-difluorobenzonitrile in 20 mL of DMSO was heated at 100 C. for 16 h. The mixture was cooled to room temperature, acidified with 1M HCl, washed with ether (3*), made basic with conc. ammonium hydroxide, and extracted with ethyl acetate (3*). The combined organic layers were washed with water (3*), dried (magnesium sulfate), filtered and evaporated. Purification by silica gel MPLC with 90:10 chloroform:methanol gave 0.51 g of (7RS,9aSR)-7-hydroxymethyl-2-(2-cyano-4-fluorophenyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine.

According to the analysis of related databases, 64248-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US5852031; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

935-02-4, name is 3-Phenylpropiolonitrile, 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. HPLC of Formula: C9H5N

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
Nitrile – Wikipedia,
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Electric Literature of 858523-37-2, 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. 858523-37-2 name is (4-Bromo-2-methoxyphenyl)acetonitrile, 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.

Preparation 6(S)-3-(4-Bromo-2-hydroxy-phenyl)-pyrrolidine-l-carboxylic acid tert-bntyl ester The synthetic procedure described in this Preparation was carried out according to the process shown in Scheme G. EPO SCHEME GStep 1 (4-Bromo-2-methoxy-phenyl)-acetic acid; A solution of NaOH (5.72 g, 143 mmol) in water (29 mL) was added to a solution of (4- bromo-2-methoxy-phenyl)-acetonitrile (10.2 g, 45.1 mmol) in MeOH (100 mL). The reaction mixture was heated at reflux for 18 hours. The solvent was evaporated under reduced pressure and water was added. The aqueous mixture was washed with diethyl ether, and the aqueous layer was acidified by addition of aqueous HCl (2 M) to pH 1. The aqueous mixtuer was then extracted with EtOAc, and the combined organic extracts were washed with brine, dried OVCrNa2SO4, filtered, and evaporated under reduced pressure to give 9.49 g (86% yield) of (4-bromo-2-methoxy-phenyl)-acetic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-Bromo-2-methoxyphenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/55847; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, 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 17 3-Bromo-6-fluoro-2-methylbenzonitrile To a cooled (0 C) solution of 2-fluoro-6-methylbenzonitrile (5.0 g, 37 mmol) in 100 mL of concentrated H2S04 was added NBS (6.93 g, 38.9 mmol). Then the mixture was stirred at 0 C for 3 hrs and poured into ice-water (1 L). The solution was extracted three times with EtOAc (200 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel fash chromatography to give 3-bromo-6-fluoro-2-methylbenzonitrile. 1H-NMR (400 MHz, CDC13) delta ppm 7.71-7.74 (m, 1H), 6.95 (t, J=8.6 Hz, 1H), 2.62 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-methylbenzonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
Nitrile – Wikipedia,
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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. 17626-40-3, name is 3,4-Diaminobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H7N3

General procedure: To a methanolic solution of the hydrogenated product 1 (0.40 g, 3.06 mmol), equivalent amount of 2,4-difluorobenzaldehyde (0.44 mL, 3.06 mmol) and half equivalent of aqueous solution of Na2S2O5 (0.29 g, 1.53 mmol in 3 mL H2O) were added. The resulting solution was stirred at reflux for 5 h, and filtered through a bed of Celite. The filtrate was concentrated under reduced pressure and residue was purified by column chromatography (eluent pet. ether/EtOAc, 7:3). The pure product was isolated as a solid (0.46 g, 1.83 mmol 65% yield)

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Manish; Tandon, Vibha; European Journal of Medicinal Chemistry; vol. 46; 2; (2011); p. 659 – 669;,
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Electric Literature of 71825-51-9, 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. 71825-51-9 name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, 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.

which is subsequently reduced to the amine 2-3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-2-(4-nitrophenyl)propanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; INTELLIKINE, LLC; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2012/116237; (2012); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 26830-95-5, 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 26830-95-5 as follows.

Step 1. Preparation of 2-amino-4-methyl-benzonitrile (B10-1): A solution of 4-methyl-2-nitrobenzonitrile (10 g, 61.72 mmol) in ethanol (200 mL) was charged to a Parr reactor and treated with 10% Pd/C (1 g). The contents of the reactor were then hydrogenated at 50 Psi hydrogen pressure 25 C. for 90 minutes. The reaction mixture was filtered through a Celite bed and washed with ethanol. The combined filtrates were the concentrated to provide B10-1. Yield: 8.5 g. 1H NMR (CDCl3): delta 7.28 (s, 1H), 6.5-6.62 (m, 2H), 4.2-4.42 (broad, 2H) and 2.3 (s, 3H). Mass: (M-1) 132 calculated for C8H8N2. The product was used without further purification to prepare B10-2 in the step described below.

According to the analysis of related databases, 26830-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US2009/54395; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 90110-98-8, 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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 0-10C, anhydrous ethanol (27 mL) was slowly added dropwise into a mixture of selenium powder (2.7 g, 34.2 mmol) and sodium borohydride (1.57 g, 41.5 mmol), then heated to room temperature and stirred for 30 min, and then added with pyridine solution (7.2 mL) containing 3-bromo-4-isopropylthiomethyl benzonitrile (63) (1.8 g, 8.49 mmol). The reaction solution was heated until reflux occurred, slowly added dropwise with 2M hydrochloric acid solution (18 mL) and then stirred under reflux for 1 h. A TLC analysis indicated that the reaction was completed. The solution was cooled to room temperature, added with a proper amount of water and then extracted with ethyl acetate (30 mL¡Á3). The organic phase was respectively washed with 2M hydrochloric acid (20 mL) and saturated saline solution (20 mL), and dried with anhydrous sodium sulfate. The solvent was removed by means of reduced pressure distillation, so as to obtain pink 3-bromo-4-hydroxymethyl selenobenzamide (64) (1.98 g), with a yield of 79.6%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Atom Bioscience and Pharmaceutical Co. Ltd.; SHI, Dongfang; FU, Changjin; WU, Jie; LIU, Jun; EP2927219; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 7153-22-2, 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. 7153-22-2, name is Ethyl 4-cyanobenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Hydrogenation of 1 mmol of hexyl hexanoate under 20 bar at 100C in toluene, resulted in 99% yield of hexanol (Entry 1). Under the same conditions ethyl butyrate was hydrogenated to give 98% yield of butanol and 91 % yield of ethanol after 50 hours (Entry 2). When the reaction was performed at shorter reaction time (22 hours, Entry 2bis), small amounts of ethyl acetate and butyl butanoate were also formed, attributed to a transesterification reaction with the formed ethanol and butanol. Cyclohexylmethyl acetate gave 99% yield of cyclohexylmethanol and 60% yield of ethanol (Entry 3), and no transesterification products were observed. Hydrogenation of the secondary aliphatic ester heptan-2-yl acetate resulted in 98% yield of heptane-2-ol and 57% yield of ethanol (Entry 4). Ethyl 3-phenylpropanoate was smoothly hydrogenated, rendering 99% yield of 3-phenylpropan-l-ol and 70% yield of ethanol after 21 hours (Entry 5). Similarly, ethyl 3- phenylpropanoate gave 99% yield of phenyknethanol and 74% yield of butanol after 22 hours (Entry 6). In order to get full hydrogenation of benzyl benzoate longer reaction time was needed (43 hours, 99% yield benzyl alcohol, Entry 7). Similarly, methyl benzoate gave 96% yield of benzyl alcohol and 63 % of methanol after 50 hours (Entry 8). epsilon-Caprolactone was smoothly and quantitatively hydrogenated to 1 ,6-hexanediol (99% yield, Entry 9). The activated benzyl trifluoroacetate gave 99% yield of benzyl alcohol and 78% of 2,2,2- trifluoroethanol (Entry 10), and no secondary products where observed. Gratifyingly, allyl trifluoroacetate gave 97% yield of 2,2,2-trifluoroethanol and 96% of allyl alcohol (Entry 1 1), showing high chemoselectivity to ester hydrogenation over C=C hydrogenation. Hydrogenation of ethyl 4-isocyano-benzoate required an increase of precatalyst loading to 3%, probably due to competing nitrile coordination, and resulted in 61 % yield of (4-isocyanophenyl)methanol and 66% yield of ethanol, with no hydrogenation of the nitrile group detected (Entry 12).

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, Ethyl 4-cyanobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YEDA RESEARCH AND DEVELOPMENT CO. LTD.; NERUSH, Arkadi; MILSTEIN, David; VOGT, Matthias; MUKHERJEE, Arup; ESPINOSA-JALAPA, Noel Angel; CHAKRABORTY, Subrata; (194 pag.)WO2017/137984; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 328-87-0, A common heterocyclic compound, 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, molecular formula is C8H3ClF3N, 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 I Into 100 ml. of ethanol is added 12.4 g. (0.10 moles) of benzylmercaptan. While nitrogen is bubbled into the solution, 100 ml. of a 1 molar sodium ethoxide in ethanol solution is added. The solvent is evaporated and 100 ml. of anhydrous dimethylformamide is added to the crude solid sodium mercaptide. To the resulting solution is then added 21 g. (0.10 moles) of 4-chloro-3-cyanobenzotrifluoride. The reaction mixture is stirred under nitrogen at room temperature for 1/2 hour and then poured into about 800 ml. of ice-water. After stirring this mixture for 5 minutes, it is extracted with four 200 ml.-portions of ether. The extracts are combined, dried over anhydrous sodium sulfate and evaporated to provide, after drying under high vacuum, a pale yellow oil that crystallizes to a solid upon standing. The yield of crude 2-benzylthio-5-trifluoromethylbenzonitrile is 27.4 g. (94 percent).

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US3954994; (1976); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts