Tag: M.W=100-200

Electric Literature of 76469-88-0,Some common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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.

Methyl 4-(cyanomethyl)benzoate (25g, 0.14mol) dissolved in 300mL methanol was add 160mL 1N NaOH and refluxed for3 hours. Most of the solvent was removed in vacuo. The residue was added 500mL water and acidified to pH 2-3 with concentrated HCl. The generated solid was filtered, washed with water and dried to give the title compound as white solid (21.2g, 92.2%): 1H NMR (400MHz, DMSO-d6) delta 12.89 (brs, 1H), 7.87 (d, J=8.2Hz, 2H), 7.37 (d, J=8.2Hz, 2H), 3.45 (s, 2H); MS(EI): 161[M]+.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Danqi; Shen, Aijun; Li, Jian; Shi, Feng; Chen, Wuyan; Ren, Jing; Liu, Hongchun; Xu, Yechun; Wang, Xin; Yang, Xinying; Sun, Yiming; Yang, Min; He, Jianhua; Wang, Yueqin; Zhang, Liping; Huang, Min; Geng, Meiyu; Xiong, Bing; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 765 – 781;,
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Adding a certain compound to certain chemical reactions, such as: 77326-36-4, name is 2-Amino-6-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 77326-36-4, Formula: C7H5FN2

NaOMe(25%wtinMeOH,325muL,1.42mmol,1.1eq.)wasaddedtoasolutionof2-amino-6-fluorobenzonitrile (176 mg, 1.29 mmol, 1.0 eq.) in DMF (1.00 mL) at roomtemperature, and stirred for 18 hours. The solution was concentrated in vacuo and theresidue stirred with H2O (10 mL) to give a beige precipitate. This was filtered underreducedpressure,theresiduedissolvedinEtOAcandconcentratedinvacuo,tituratedwithhexanes before remaining solvent was removed in vacuo giving 2-amino-6-methoxybenzonitrile(158mg,1.07mmol,83%)asabeigeamorphoussolid;mp143-145C,lit.136-140C.13

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Sutherell, Charlotte L.; Ley, Steven V.; Synthesis; vol. 49; 1; (2017); p. 135 – 144;,
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Electric Literature of 51762-67-5, 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. 51762-67-5 name is 3-Nitrophthalonitrile, 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.

With 3-hydroxybenzoic acid (15mmol) and 3-nitro-phthalonitrile (15mmol) as reactants, the solvent is anhydrous DMSO (30ml), potassium carbonate (45mmol) under nitrogen and the presence, stirred at room temperature The reaction 30 hours, by thin layer chromatography to monitor the end of reaction.The reaction mixture was diluted with sand core funnel filtration, the filtrate was collected, and the filtrate was added to 500ml of ice water mixture, adjusted with 1M hydrochloric acid solution until the solution was acidic precipitation heavy precipitate, was allowed to stand, an organic microporous membrane, repeated washing more times until the solution was neutral, the solid was collected and lyophilized to give a white solid, further use DMF- water purified by recrystallization to give a white desired product, a yield of about 78%.

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

Reference:
Patent; Fuzhou University; Huang, Bindong; Chen, Xingwei; Zheng, Qiaofeng; Ke, Meirong; (19 pag.)CN105622682; (2016); A;,
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Reference of 4640-67-9, 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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 0.11 g (0.67 mmol) 3 -(4-fluoro -phenyl)- 3-oxo-propionitrile in 4 ml ethanol was added 0.06 ml (0.67 mmol) cyclopentanone, 22 mg (0.67 mmol) sulfur, and 0.06 ml (0.67 mmol) morpholine. The mixture was heated at 60 0C for 2 h, and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 0.17 g (98%) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-fluoro- phenyl)-methanone as a red solid. ES-MS m/e (%): 262 (M+H+, 100).

The synthetic route of 3-(4-Fluorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2006/63732; (2006); A1;,
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Related Products of 4640-67-9, 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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: LB medium supplemented with 30 mug/mL kanamycin was inoculated with a single colony of E. coli (containing the appropriate overexpressed gene) and shaken 15 h at 37 C. This preculture was diluted 1:100 into 30 mL of the same medium and shaken 2.5 h at 37 C with a stir rate of 220 rpm. Upon reaching an O.D.600 = 0.5 the cell culture was cooled to 20 C, and isopropylthio-beta-D-galactoside was added to a final concentration of 100 muM and shaken for 2 h. The beta-keto nitrile substrate was added to a final concentration of 2 mM using a concentrated acetonitrile solution. (Ethanol and methanol solutions were avoided due to an increase in alkylation). This reaction was allowed to shake at 220 rpm for 12 h. The reaction was then gently extracted with methylene chloride (2 mL) and analyzed by chiral GCMS.

The synthetic route of 3-(4-Fluorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nowill, Randall W.; Patel, Trisha J.; Beasley, David L.; Alvarez, Jose A.; Jackson III, Elizah; Hizer, Todd J.; Ghiviriga, Ion; Mateer, Scott C.; Feske, Brent D.; Tetrahedron Letters; vol. 52; 19; (2011); p. 2440 – 2442;,
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Adding a certain compound to certain chemical reactions, such as: 135748-35-5, name is 4-Chloro-2,5-difluorobenzonitrile, 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 135748-35-5, Recommanded Product: 4-Chloro-2,5-difluorobenzonitrile

General procedure: Hydrogen chloride gas was passed through a solution of 4-chlorobenzonitrile (9b, 25.0 g) in chloroform (350 mL) and ethanol (100 mL) at -78 C for 0.5 h. Then the solution was warmed up to room temperature, and stirred at room temperature overnight. The solution was evaporated in vacuo, and the resulting residue was dissolved with ethanol (500 mL). To the solution was added ammonium carbonate (90.0 g), and the reaction mixture was stirred at room temperature for 3 days. To the mixture was added water (300 mL), and ethanol was removed by concentration in vacuo. The resulting solid was collected by filtration, washed with water and dried in vacuo to give 12b (25.4 g, 71%) as a white solid.

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, 4-Chloro-2,5-difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Misawa-Mukai, Hana; Hamaguchi, Wataru; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5235 – 5246;,
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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. 114344-60-4, name is 2-Amino-3-bromobenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-Amino-3-bromobenzonitrile

xample 11 – Synthesis of Compound 15; A solution of 1.39 g (7.04 mmol) 2-amino-3-bromo-benzonitrile (synthesis described in J. B. Campbell and T. W. Davenport, Syn. Commun. 19, 2255 [1989]) in 14 ml 1 – butanol was treated with 1.14 g (14.1 mmol) triazine and 1.2 ml acetic acid and heated to 110 C. The resulting solution was stirred for 4 days at this temperature. The reaction mixture was cooled to room temperature and evaporated. The residue was crystallized from tert.butyl-methyl-ether yielding 8-bromo-quinazolin-4-ylamine as brown solid; HPLC/MS: 1.00 min, [M+H] 224/226

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; JONCZYK, Alfred; HOELZEMANN, Guenter; AMENDT, Christiane; ZENKE, Frank; WO2012/595; (2012); A1;,
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Application of 63069-50-1, 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. 63069-50-1 name is 4-Amino-3-fluorobenzonitrile, 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: To the solution of 19 chloro-6, 7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (0.22mmol) and substituted anilines (0.22mmol) in 46 1,4-dioxane (2mL) was added 47 Pd2(dba)3 (0.05mmol), X-Phos (0.05mmol) and 48 Cs2CO3 (0.55mmol). The reaction was heated to reflux under nitrogen gas for overnight. Then the mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the 20 product. 4.1.8 50 tert-butyl 4-((2-((4-(methylsulfonyl)phenyl)amino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (12)

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

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
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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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Hydroxymethyl)benzonitrile

Synthesis was performed using a PE Biosystems (Applied Biosystems) Solaris 530 organic synthesizer. 4-Cyanobenzyl alcohol (0.6 mmol) was dissolved in 3 mL DMA then transferred to a 4 mL vial containing 0.5 mmol of Dess-Martin Reagent. The vial was shaken to ensure mixing then used directly. A round bottom flask was charged with 3 equivalents of MP-BH3CN. The block was placed on the Solaris 530 and 1 equivalent of 5-(4-amino-phenyl)-6-ethyl-pyrimidine-2,4-diamine from Example 1C (dissolved in 1:1 MeOH/CH2Cl2) was added to the round bottom flask. The oxidized 4-cyanobenzyl alcohol was then added (2 eq) followed by 3 equivalents of a solution of HOAc in 1:1 MeOH/CH2Cl2. The block was then heated to 55C overnight. The mixture was transferred with MeOH to a 20 mL vial containing scavenger resins PS-TsNHNH2 and MP-Carbonate (3 eq each). The resins were filtered and the product concentrated. Purification by Reverse Phase HPLC to provided the titled compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 0.94 (t, J=7.49 Hz, 3H), 2.11 (q, J=7.59 Hz, 2H), 4.38 (d, J=5.93 Hz, 2 H), 5.32 (s, 2H), 5.77 (s, 2H), 6.44 (t, J=5.93 Hz, 1H), 6.61 (d, J=8.42 Hz, 2 H), 6.85 (d, J=8.42 Hz, 2H), 7.58 (d, J=8.11 Hz, 2H), 7.80 (d, J=8.11 Hz, 2H);MS (ESI) positive ion 345(M+H)+.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kosogof, Christi; Liu, Bo; Liu, Gang; Liu, Mei; Nelson, Lissa T. J.; Serby, Michael D.; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; US2005/171131; (2005); A1;,
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Related Products of 115279-57-7, A common heterocyclic compound, 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, molecular formula is C10H12N2, 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: To a solution of 6 (1.0 equiv) in acetic acid (2 mL/1 mmol substrate)AcONa (1.4 equiv) and substituted aniline (1.0 equiv), suchas 2 or 3-trifluoromethylaniline, were added. The resultant mixturewas stirred for 0.5 h at room temperature and quenched withwater. After the rude product was totally precipitated, it was filtered,washed with water and dissolved in DCM. The solutionwas then washed with saturated NaHCO3 solution, brine and driedover anhydrous Na2SO4. Following removal of solvent in vacuo, theresidue was purified via flash column chromatography using EA/PE(1:6) as eluent to afford corresponding ethyl 6-bromo-4-anilino-3-carboxylate quinoline derivative 7a or 7b as light yellow solid. 4.1.4.1 Ethyl 6-bromo-4-((4-(2-cyanopropan-2-yl)phenyl)amino)quinoline-3-carboxylate (7a) Light yellow solid; yield: 83%; ESI-MS: m/z = 438 [M+H]+.

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:
Article; Ma, Xiaodong; Lv, Xiaoqing; Qiu, Ni; Yang, Bo; He, Qiaojun; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 23; 24; (2015); p. 7585 – 7596;,
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