Month: January 2021

Application of 1885-38-7, 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. 1885-38-7 name is (E)-Cinnamonitrile, 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.

General procedure: In a Schlenck flask filled with gaseous carbon dioxide, to a stirred THF (1.5 mL) solution of the alpha,beta-unsaturated compound 1 (0.25 mmol) and bis(acetylacetonato)cobalt(II) (conditions A: 3.2 mg, 5 mol %; conditions B: 6.4 mg, 10 mol %) was added a 1.0 M n-hexane solution of diethylzinc (conditions A: 0.5 mL, 2 equiv; conditions B: 1.0 mL, 4 equiv) at 0 C, then the reaction mixture was stirred at 20 C for 1-48 h. After checking the completed reaction by TLC analysis, the reaction mixture was quenched with a 1.0M hydrochloric acid diethyl ether solution (conditions A: 1.5 mL, 6 equiv; conditions B: 3.0 mL, 12 equiv) at 0 C. The organic layer was extracted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by silica gel column chromatography (Hexanes:AcOEt:HCOOH = 1:1:0.003) to afford the desired carboxylic acid 2. The resulting compound was diluted with a mixed solution (6.25 mL, diethyl ether:MeOH = 5:1) and methylated with trimethylsilyldiazomethane in n-hexane (ca. 0.6M solution, (1.04 mL, 2.5 equiv)). After purification by chromatography on silica gel, the corresponding methyl carboxylate was isolated.

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

Reference:
Article; Hayashi, Chika; Hayashi, Takuo; Yamada, Tohru; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 862 – 870;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6393-40-4, name is 4-Amino-3-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 6393-40-4, Recommanded Product: 6393-40-4

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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:
Article; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 67832-11-5, 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2.5 M n-butyllithium in hexanes(6.7 mL, 16.8 mmol) was added to anhydrous THF (15 mL) at -78 C. A solution of 4-bromo-2-methylbenzonitrile 21 (3.0 g, 15.3 mmol) in THF (15 mL) was then added dropwise and allowed to stir for 30 min. Dry ice (solid CO2) was added and the solution was allowed to stir 1 h while warming to room temperature. The reaction was then concentrated in vacuo and the resulting residue was triturated in ether and filtered. The solid was dissolved in EtOAc and washed with 2 M HCl and brine. The organic layer was isolated, dried over MgSO4, concentrated in vacuo, then triturated in ether/ hexane and dried under high vacuum. Obtained 4-cyano-3-methylbenzoic acid 22 (1.5 g, 60.8% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta (ppm) 8.18 (s, 1H), 8.02-8.09 (m, 1H), 7.75-7.81 (m, 1H), 2.61 (s, 3H).

The synthetic route of 4-Bromo-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yestrepsky, Bryan D.; Xu, Yuanxi; Breen, Meghan E.; Li, Xiaoqin; Rajeswaran, Walajapet G.; Ryu, Jenny G.; Sorenson, Roderick J.; Tsume, Yasuhiro; Wilson, Michael W.; Zhang, Wenpeng; Sun, Duxin; Sun, Hongmin; Larsen, Scott D.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1880 – 1897;,
Nitrile – Wikipedia,
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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. 3441-01-8, name is 3-Cyanobenzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Cyanobenzamide

Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 447 muiotaetaomicron), 3-cyanobenzamide (163 mg, 1.12 mmol), Tripotassium phosphate (133 mg, 626 muiotaetaomicron), tBuBrettPhos (13.0 mg, 26.8 muiotaetaomicron), and tBuBrettPhos Pd G3 (22.9 mg, 26.8 muiotaetaomicron) were dissolved in l-Methoxy-2-propanol (5.0 ml, 52 mmol). The mixture was stirred at 110 ¡ãC for 16 h and then purified via reverse phase chromatography (Method: Reprosil C18; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / solvents: A = water (0,01percent formic acid), B = Acetonitrile / gradient 0.00-4.25 min = 20percentB, 4.50min = 30percentB, 19.00-22.50min = 100percentB, 22.75-25.00min = 20percentB) which afforded the product after drying in vacuo. The obtained amout was 130 mg (100 percent purity, 57 percent of theory). LC-MS (Method 1): Rt = 1.15 min; MS (ESIpos): m/z = 513 [M+H]+

The synthetic route of 3441-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 6587-24-2, name is Methyl 2-cyanobenzoate, molecular formula is C9H7NO2, 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. category: nitriles-buliding-blocks

Methyl 2-cyanobenzoate 1 (16.10 g, 100 mmol) was dissolved with stirring in a freshly prepared solution of sodium methoxide in dry MeOH (120 mL) obtained by dissolving sodium metal (0.46 g, 20 mmol). Dry ammonia gas was bubbled with stirring through the obtained solution for 1h at 0 C. Further, ammonia gas was bubbled for an additional 2 h while heating. After standing the mixture in refrigerator overnight the resulting crystals of 3-amino-1H-isoindol-1-one 2a were filtered, washed with cold MeOH (25 mL) and dried in air. Filtrate was evaporated to 50 mL volume and cooled in refrigerator. Crystalline precipitate was filtered, washed with cold MeOH (10 mL), and dried in air to provide additional amount of title compound 2a; colorless crystals (12.85 g, 88 %), mp 203-204 C (Lit. 203-204 C [3]).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6587-24-2, its application will become more common.

Reference:
Article; Tkachuk, Volodymyr; Merkulova, Vladyslava; Omelchenko; Arrault, Axelle; Hordiyenko, Olga; Tetrahedron Letters; vol. 60; 30; (2019); p. 1959 – 1963;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 127946-77-4, 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. 127946-77-4 name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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.

To a solution of 2-bromo-1-(4-fluorophenyl)ethanone (3.0 g, 13.82 mmol) and DIPEA (7.24 mL, 41.5 mmol) in NMP (55.3 mL) was added 1-aminocyclopropanecarbonitrile, HCl (1.859 g, 15.20 mmol) and the reaction mixture was stirred overnight at RT. Since the starting material was not completely consumed, the mixture was heated in an oil-bath at 70 C. for 1 h, cooled to RT, diluted with water and extracted with EtOAc (2¡Á50 mL). The combined organic layers were washed with brine and dried over anhydrous MgSO4, filtered. The filtrate was concentrated under reduced pressure (water-bath temp.25 C.) and the residue was purified by silica gel chromatography (40 g RediSep column, eluting with 30% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford intermediate 188A? (1.66 g, 54.97% yield) as an oil. MS (ES): m/z=219.15 [M+H]+; HPLC Ret. Time min. 2.903 (HPLC Method E).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; Bristol-Myers Squibb Company; Kinsella, Todd; Gelman, Marina; Hong, Hui; Darwish, Ihab S.; Singh, Rajinder; Yu, Jiaxin; Borzilleri, Robert M.; Velaparthi, Upender; Liu, Peiying; Darne, Chetan; Rahaman, Hasibur; Warrier, Jayakumar Sankara; (311 pag.)US2016/257690; (2016); 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. 6629-04-5, name is N-Cyanoacetylurethane belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Cyanoacetylurethane

A mixture of 6-(4-amino-2,6-dichloro-phenylsuhcanyl)-4-isopropyl-2H-pyridazin-3-one (85) (3.40 g, 10.4 mmol) in water (135 mL) and concentrated hydrochloric acid (68 mL) cooled to 00C was treated with a solution of sodium nitrite (853 mg, 12.36 mmol) in water (7.0 mL) via Pasteur pipette under the surface of the reaction mixture. This was followed by a EPO water rinse (1.0 mL) of the Pasteur pipette. The resulting yellow mixture was stirred at 00C for 30 min. More concentrated hydrochloric acid (7.0 mL) was added. The reaction was stirred at 00C for an additional 1.3 h. The solids were removed by filtration through filter paper and were rinsed with water. The clear, yellow diazonium salt solution of the filtrate was quickly poured into a solution of cyanoacetylurethane (1.77 g, 11.33 mmol), pyridine (75 mL) and water (204 mL) cooled to 00C. Upon mixing, orange-red solids immediately formed. This mixture was stirred at 00C for 1 h. At this time, the solids were collected by filtration through filter paper. The solids were washed with water, air-dried under house vacuum for 2 h, and then dried under vacuum to afford (2-cyano-2-{ [3,5-dichloro-4-(5- isopropyl-6-oxo- 1 ,6-dihydro-pyridazin-3-ylsulfanyi)-phenyi] -hydrazono } -acetyl)-carbamic acid ethyl ester (86) (2.98 g, 58%) as an orange solid; ES(+)-HRMS m/e calcd for Ci9Hi8Cl2N6O4S (M+H)+ 497.0560, found 497.0559. Exact Mass = 496.0487; Molecular weight = 497.36

The synthetic route of 6629-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/9913; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 103146-25-4, 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 103146-25-4 as follows.

Experiment 9: The general procedure of Experiment 2 was applied. Additionally a small amount of water (0.05 V) was added to the 4-[4-(dimethylamino)-l-(4′-fluorophenyl)- l-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile free base solution in 1-propanol. An exemplary batch gave molar yield: 33.0%; enantiomeric purity: 99.1% S.

According to the analysis of related databases, 103146-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 115279-73-7, 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. 115279-73-7 name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, 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.

To a 250 ml four-necked flask equipped with a stirrer, thermometer, and reflux condenser.Add 150 g of diethyl malonate, 18.6 g (0.1 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile II, and de-alcoholization reaction at 105-110 C for 4 hours (first amidation reaction) Excessive distillation of diethyl malonate was carried out under reduced pressure, cooled to 60-70 C, 13.0 g (0.12 mol) of 4-aminomethylpyridine IV was added, and the dealcoholization reaction was carried out for 4 hours at 110-115 C (second time) Amidation reaction). After cooling to 30-40 C, 80 g of isopropanol was added to the residue, recrystallized, filtered and dried to give 33.1 g of N-(4-pyridine)methyl-N’-4-(1-cyanocyclopentane) Phenylmalonamide, yield 91.3%, liquid phase purity 99.9%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Aminophenyl)cyclopentanecarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Fan Yansen; Ju Lizhu; (9 pag.)CN109810052; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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.

General procedure: The synthesis was carried out by using the synthetic method c. To a solution of 3-aminobenzonitrile (0.603 g, 3.39 mmol)and DIPEA (1.09 g, 8.46 mmol) in dichloromethane (40 mL) was added picolinoyl chloride HCl salt (0.562 g, 3.39 mmol). The mixture was stirred for 4 h. The mixture solution was injected into a silica-gel column (40 g) andpurified by CombiFlash eluting with dichloromethane and ethyl acetate to give the product as a white solid (630.2 mg, 2.82 mmol, 83.3% yield)

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Zhaoda; Kil, Kun-Eek; Poutiainen, Pekka; Choi, Ji-Kyung; Kang, Hye-Jin; Huang, Xi-Ping; Roth, Bryan L.; Brownell, Anna-Liisa; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3956 – 3960;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts