Author: tianli

Adding a certain compound to certain chemical reactions, such as: 10406-25-4, name is 4-(Aminomethyl)benzonitrile, 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 10406-25-4, Recommanded Product: 4-(Aminomethyl)benzonitrile

1. Model canadense amide quinones (DCA – CONH – 02) preparation, comprising the following steps:

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

Reference:
Patent; Guangdong University of Technology; Zhao Suqing; Zhang Bingjie; Feng Dongyan; Fang Yinglin; Wu Ke; Ling Huaying; Tan Qiting; Chen Yanting; Yang Yang; Zhao Jiawei; Ma Zhuolin; Hong Weiqian; (24 pag.)CN109651183; (2019); A;,
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Electric Literature of 1009-35-4, The chemical industry reduces the impact on the environment during synthesis 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

A mixture of 4-fluoro-3-nitrobenzonitrile (5.0 g, 30.1 mmol) and Fe powder (5.05 g, 90.3 mmol) in AcOH (100 mL) was heated at 80 C for 1 hour under N2. Then the solvent was removed under vacuum and water (200 mL) was added to the residue. The solution was adjusted to pH 6 by addition of Na2C03 and extracted with DCM (2 x 200 mL). The organic layers were combined, dried over Na2S04, filtered and concentrated to yield 3- amino-4-fluorobenzonitrile (48), which was used without further purification. MS m/z 137.0 (M+1 ) +. To a stirring suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (3.0 g, 18.5 mmol) in anhydrous dichloromethane (50 mL) at 0 C was added dropwise oxalyl chloride (4.84 mL, 55.5 mmol). Then, three drops of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 15 minutes. The solvent was concentrated and the crude solid was added to a stirring solution of 3-amino-4- fluorobenzonitrile (48) (2.5 g, 18.5 mmol) in anhydrous pyridine (50 mL) at room temperature. The reaction was stirred for 20 minutes and quenched with water (200 mL) with stirring for another 10 minutes. Then the precipitate was filtered and dried in air to yield N-(5-cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49). 1 H NMR (400MHz, c/6-DMSO) delta 10.40 (s, 1 H), 9.43 (td, J = 1 .2, 6.8 Hz, 1 H), 8.63 (s, 1 H), 8.21(dd, J = 2.0, 7.2 Hz, 1 H), 7.78-7.84 (m , 2H), 7.54-7.63 (m , 2H), 7.22 (dt, J = 1 .2, 6.8, 1 H). MS m/z 281 .1 (M+1 ) +. NH2OH (10 mL, 32.1 mmol) was added in one portion to a stirred suspension of N-(5- cyano-2-fluorophenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (49) (3.6 g, 12.85 mmol) in EtOH (100 mL). The resulting suspension was heated at 70 C for 3 hours and then the solvent was removed to yield N-(2-fluoro-5-(N’- hydroxycarbamimidoyl)phenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (50). 1 H NMR (400MHz, c/6-DMSO) delta 10.21 (s, 1 H), 9.70 (s, 1 H), 9.45 (td, J = 1 .2, 7.2 Hz, 1 H), 8.61 (s, 1 H), 7.95 (dd, J = 2.4, 7.6 Hz, 1 H), 7.79 (td, J = 1 .2, 8.8 Hz, 1 H), 7.51 -7.60 (m , 2H), 7.31 -7.37 (m, 1 H), 7.19 (dt, J = 1 .2, 6.8, 1 H), 5.88 (s, 2H). MS m/z 314.1 (M+1 ) +.

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

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
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These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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. name: 4-(Trifluoromethyl)phenylacetonitrile

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

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

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
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Electric Literature of 1572-52-7, 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. 1572-52-7, name is 2-Methylenepentanedinitrile, This compound has unique chemical properties. The synthetic route is as follows.

REFERENCE EXAMPLE 1 3-(3,4-Dichlorophenylthio)-2-(2-methoxycarbonylethyl)propionic acid A mixture of 3,4-dichlorobenzenethiol (3.00 ml), methyleneglutaronitrile (2.57 ml), ethanol (25 ml), and triton B (40% methanol solution, 10 drops) was refluxed for 4 hours. After the reaction mixture was concentrated in vacuo, the resulting residue was dissolved in chloroform, washed with water, and dried over MgSO4. The solvent was evaporated at reduced pressure, and the residue was recrystallized from diethyl ether-hexane to give 6.14 g of 2-(3,4-dichlorophenylthiomethyl)glutaronitrile. Melting point: 53-55 C. IR (KBr): nuCN 2240 cm-1

The chemical industry reduces the impact on the environment during synthesis 2-Methylenepentanedinitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; US5145869; (1992); A;,
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Electric Literature of 115279-73-7, The chemical industry reduces the impact on the environment during synthesis 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, I believe this compound will play a more active role in future production and life.

In a 500 ml four-necked flask equipped with a stirrer, thermometer and distillation system, add 100 g of N,N-dimethylformamide, 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V), 0.2 g of cuprous chloride. While maintaining the internal temperature between 95 and 100 C, 12.2 g (0.05 mol) of methyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV1) prepared in Example 3 and 30 g N,N-dimethylformamide were added dropwise. The solution of N,N-dimethylformamide is added dropwise in about 1 hour, after which the reaction is stirred at 100-105 C for 4 hours, and the formed methanol is distilled off, the reaction is completed, the temperature is lowered to 20-25 C, and the filter cake is used for filtration. After washing with 20 g of N,N-dimethylformamide, the filtrate was combined, and N,N-dimethylformamide was evaporated under reduced pressure. The residue was crystallized from methyl t-butyl ether, filtered and dried. 18.3 g of a white solid powder of agingatin (I) was obtained in a yield of 92.2%, a liquid phase purity of 99.96% and a melting point of 158.5-160.0 C.

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, 1-(4-Aminophenyl)cyclopentanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
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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. 2032-34-0, name is 3,3-Diethoxypropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2032-34-0

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

According to the analysis of related databases, 2032-34-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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Application of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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26830-95-5, name is 4-Methyl-2-nitrobenzonitrile, 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. Safety of 4-Methyl-2-nitrobenzonitrile

Example 17: Alternative preparation of 4-cyano-3-nitro-benzoic acid; Under an inert atmosphere, periodic acid (492 g, 2.17 mol) was dissolved in acetonitrile (7.7 1) with vigorous stirring, and then, after 15 minutes chromium(VI) oxide (25 g, 0.25 mol) and 4-methyl-2-nitro-benzonitrile (100 g, 0.62 mol) were added successively. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was decanted and the supernatant filtered. The filtrate was concentrated and the residue partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (150 g). The filtrate was extracted twice with dichloromethane and was then acidified by addition of aqueous hydrochloric acid (4N) to pH 1. The acidified filtrate was then extracted three times with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. This residue was partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (26.67 g). Total yield: 150 g + 26.67 g = 176.67 g; 74.5 % yield.

The synthetic route of 26830-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2008/74427; (2008); A1;,
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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. 4623-24-9, name is 2-(3-Aminophenyl)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(3-Aminophenyl)acetonitrile

To a cold (0 C) solution of Intermediate BD (500mg, 3.78 mmol) and triethylamine (0.63 mL, 4.48 mmol) in dichloromethane (10 mL) was added slowly methanesulfonyl chloride (0.35 mL, 4.49 mmol) over 5 minutes. After the addition was complete, the reaction mixture was allowed to reach room temperature and stirred for 2 hours. The reaction mixture was diluted with dichloromethane (10 mL), washed with water (2 chi 20 mL) and brine (10 mL), dried over anhydrous Na2S04, and the solvent was removed to afford the crude product. This material was purified by column chromatography (silica gel 100-200 mesh) using 15% ethyl acetate in petroleum ether as the eluent to afford Intermediate BE (300 mg, 38%) as a brown gum. ‘H NMR (CDCI3): delta 7.40-7.34 (m, 1H), 7.20-7.16 (m, 2H), 6.63 (bs, 1H), 3.76 (s, 2H), 3.04 (s, 3H). Mass (M-H): 187.0

The synthetic route of 4623-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); A1;,
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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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 243128-37-2

Example 59A 4-(4-trans-amino-cyclohexyloxy)-3-methoxy-benzonitrile To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (5 mL) at 0 C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then 4-fluoro-3-methoxy-benzonitrile (182 mg, 1.2 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 247 (M+H)+.

The synthetic route of 243128-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;; ; Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2005/215784; (2005); A1;,
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