Month: August 2021

Application 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.

[019Theta] A solution of 4-(2-fluoro-4-methoxyphenoxy)piperidine hydrochloride (0.785 g, 3 mmol), 4-fluoro-3-nitrobenzonitrile (0.598 g, 3.60 mmol) and K2CO3 (1.244 g, 9.00 mmol) in DMSO (9.09 mL) was stirred at 80°C overnight. Tire reaction mixture was subsequently partitioned between EtOAc and water, and the organic layer was washed with water (2 x) and dried over anhydrous Na?,SQ4. The solvent was evaporated to give the title compound as a yellow solid, which was used without further purification (1.005 g, 90percent). ESI-MS m/z [M+H] 372.3.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Nitrile – Wikipedia,
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These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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. Product Details of 6393-40-4

General procedure: To a suspension of 2-Nitroanilines 2a-2g (10mmol) in water (5mL) and hydrochloric acid (37%, 2.5mL), a solution of sodium nitrite (0.74g, 10.75mmol) in water (4mL) at 0C was added dropwise. The mixture was stirred for 1h, diluted with water (30mL) and made acid with concentrated hydrochloric acid (2mL). In the case of 2b,f the reactions were carried out at room temperature. To this solution, freshly distilled 2,5-dimethyl-3-oxo-2,3-dihydrofuran [36] (1.24g, 11mmol) was added and the mixture was stirred for 1h at room temperature. The crude residue was collected by filtration. After drying, it was purified by column chromatography using a dichloromethane/ethyl acetate mixture in gradient as eluent and recrystallized from ethanol.

The synthetic route of 4-Amino-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mingoia, Francesco; Di Sano, Caterina; Di Blasi, Francesco; Fazzari, Marco; Martorana, Annamaria; Almerico, Anna Maria; Lauria, Antonino; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 345 – 356;,
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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 38487-86-4 as follows. Quality Control of 2-Amino-4-chlorobenzonitrile

General procedure: 2-Aminobezonitrile derivatives (1 mmol),substituted carbonyl compounds (1.5 mmol) and [Nbmd][OH] (1 mL) werestirred at room temperature. The progress of the reaction was monitored byTLC under UV light. After completion of the reaction the mixture was extractedwith ethyl acetate (3 x 10 mL) and washed with water (3 x 10 mL). Thecombined extract was dried over anhydrous Na2SO4. The filtrate wasconcentrated under reduced pressure. The product was purified by columnchromatography over silica gel using n-hexane/ethyl acetate (3:1 v/v) aseluent to get the purified product. The products were then characterized byESI-MS, 1H NMR, 13C NMR and 1F NMR spectra.

According to the analysis of related databases, 38487-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dutta, Apurba; Damarla, Krishnaiah; Kumar, Arvind; Saikia, Prakash J.; Sarma, Diganta; Tetrahedron Letters; vol. 61; 10; (2020);,
Nitrile – Wikipedia,
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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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Fluoro-3-methoxybenzonitrile

4-Fluoro-3-methoxybenzonitrile (98.2 g, 0.65 mol) was combined with 4-methyl-1 /-/- imidazole (53.4 g, 0.65 mol) and anhydrous potassium carbonate (138.2 g, 1 mol, 1.54 eq) in dimethylformamide (650 ml_), and the reaction mixture was stirred for 16 hours at 135-140 0C (internal temperature). The mixture was cooled to room temperature and filtered; the salts were washed with dichloromethane (3 x 30 ml_). The combined filtrates were evaporated in vacuo to afford a brown semisolid, which was suspended in water (500 ml_) and left to stand at 5 0C for 24 hours. The mixture was filtered, and the solid was washed with ice water (2 x 50 ml_), then dried in vacuo to afford a yellow solid (105.5 g). Crystallization from methanol (106 ml_) provided purified product (66.3 g) as yellowish crystals. These were boiled with acetone (100 ml_) for 5 minutes and the mixture was left to cool overnight. The mixture was filtered, and the crystals were washed with acetone (2 x 10 ml_) to afford the title compound as a white solid. Yield: 54.6 g, 0.256 mmol, 39%. 1H NMR (400 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.94 (s, 3H), 6.97 (m, 1 H), 7.30 (m, 1 H), 7.37 (m, 2H), 7.79 (d, J=1.4 Hz, 1 H).

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 243128-37-2.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
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Application of 59997-51-2, A common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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.

128 mL of water was added to 50 g (357 mmol) of the intermediate (c), and the mixture was stirred at room temperature, 98.2 g (785 mmol) of pivaloyl acetonitrile was added to this suspension, 12M hydrochloric acid water was added dropwise at the same temperature so that the pH became 3, The mixture was heated to an internal temperature of 50 C. and stirred at the same temperature for 6 hours. After completion of the reaction, 8N aqueous solution of calcium hydroxide was added to neutralize the solution to pH 6.4. The crystals thus precipitated were collected by filtration and washed with water until the inner temperature became 10 C. The obtained crystals were dried under reduced pressure at 60 C. and 30 mL of toluene was added to the obtained crude product In addition, it was dissolved by heating to 60 C. The resulting solution was allowed to stand at room temperature for 12 hours, and the precipitated crystals were collected by filtration, washed with cold toluene, dried at 60 C. under reduced pressure,The obtained intermediate (d) was obtained in 87.7 g (white powder, yield 69.3%), and the NMR measurement results of the obtained intermediate (d) are as follows.

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:
Patent; FUJIFILM Corporation; Tateishi, Keiichi; Sasaki, Hiroki; Nagata, Yoshiaki; (37 pag.)JP2017/61660; (2017); A;,
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Some common heterocyclic compound, 185836-35-5, name is 4-(Benzyloxy)-2-fluorobenzonitrile, molecular formula is C14H10FNO, 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. Application In Synthesis of 4-(Benzyloxy)-2-fluorobenzonitrile

To the resulting Grignard reagent was dropwise added a solution of 2-fluoro-4-benzyloxybenzonitrile (0.35 mol) in dry ether (1 l) below 20 C., and the mixture was heated for 10 hours under reflux, and then acidified with dilute sulfuric acid. Ether layer was separated, washed with water and the ether evaporated to dryness to obtain 2-fluoro-4-benzyloxy phenyl 5-methyl-heptyl ketone 896.3 g) as residue.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185836-35-5, its application will become more common.

Reference:
Patent; Chisso Corporation; US4780242; (1988); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)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 67515-59-7, Quality Control of 4-Fluoro-3-(trifluoromethyl)benzonitrile

4-Fluoro-3-(trifluoromethyl)benzonitrile (2.0g, 10.58mmol) was dissolved in dimethyl acetamide (35mL), morpholine (2.88mL, 31.73mmol) was added thereto, and the mixture was subjected to a reaction at 145C for 19 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50mL), and the organic layer was washed with an aqueous sodium hydrogen carbonate solution (50mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was crystallized with ethyl acetate (lOmL) and n-hexane (80mL) to obtain the title compound as a brown solid (2.1g).1H NMR (DMSO-d6) delta 8.17 (s, 1H), 8.08 (d, 1H), 7.58 (d, 1H), 3.71 (m, 4H), 2.99 (m, 4H).

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

Reference:
Patent; HANMI HOLDINGS CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; SON, Jung Beom; JUNG, Seung Hyun; CHOI, Wha Il; JUNG, Young Hee; CHOI, Jae Yul; SONG, Ji Yeon; LEE, Kyu Hang; LEE, Jae Chul; KIM, Eun Young; AHN, Young Gil; KIM, Maeng Sup; CHOI, Hwan Geun; SIM, Tae Bo; HAM, Young Jin; PARK, Dong-sik; KIM, Hwan; KIM, Dong-Wook; WO2011/93684; (2011); A2;,
Nitrile – Wikipedia,
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Synthetic Route of 5922-60-1, These common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, 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 2-cyano-4-chloroaniline 3g (19.6 mmol) in 30 mL of AcOH was added dropwise 1,2 mL (23.6 mmol) of bromine and the resulting mixture was stirred at 50 oC overnight. The resulting precipitate was filtered by suction on a glass frit, washed with H2O and dry under vacuum. The solid was then added by portion to a hot (50 oC) stirred solution of isoamyle nitrite 10 mL in 10 mL of DMF. After 10 min the mixture was cooled to room temperature and poured into 100 mL of HCl 3N, subject to extraction with AcOEt (3 X 40 mL), dry over Na2SO4 and concentrated on a rotary evaporator. Purification of the residue by column chromatography yielded 2.08g (49 %) 9c as a white solid1H NMR (CDCl3), d = 7.50 (t, 1H, J=2.0 Hz, CHAr); 7.60 (t, 1H, J=2.0 Hz, CHAr); 7.65 (t, 1H, J=2.0 Hz, CHAr). 13C NMR (CDCl3), d = 115.6 (1C, Cq); 166.4 (1C, Cq); 123.8 (1C, Cq); 131.0 (1C, CHAr); 133.4 (1C, CHAr).

Statistics shows that 2-Amino-5-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 5922-60-1.

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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: Step (A): To a solution of racemic (2?S,3?R,4?S,5?R)-6-chloro-4?-(3-chloro-2-fluoro-phenyl)-2?-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3?-pyrrolidine]-5?-carboxylic acid trifluoroacetic acid salt 17 (R3 = H, R1 = CH2C(CH3)3, Ref. 29) (0.2 g, 0.36 mmol) in dichloromethane (10 mL) was added diisopropylethylamine (0.18 g, 1.4 mmol), diphenylphosphinic chloride (Aldrich) (0.25 g, 1.1 mmol), respectively. The mixture was stirred at room temperature for 0.5 h, then methyl 4-amino-2-methoxybenzoate (Acros) (0.077 g, 0.43 mmol) or methyl 4-amino-3-methoxy-benzoate (Ark Pharm) (0.16 g, 0.9 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, then concentrated. The residue was purified by chromatography (3-20% of EtOAc in CH2Cl2) to give a white solid (yield 0.12 g, 54%).

Statistics shows that 4-Amino-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 177476-76-5.

Reference:
Article; Zhang, Zhuming; Ding, Qingjie; Liu, Jin-Jun; Zhang, Jing; Jiang, Nan; Chu, Xin-Jie; Bartkovitz, David; Luk, Kin-Chun; Janson, Cheryl; Tovar, Christian; Filipovic, Zoran M.; Higgins, Brian; Glenn, Kelli; Packman, Kathryn; Vassilev, Lyubomir T.; Graves, Bradford; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4001 – 4009;,
Nitrile – Wikipedia,
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34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, 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. Formula: C9H10N2

To a solution of compound 222 (1 mmol), Aldehyde/ketone (1 mmol), in THF was added NaBH3CN (2 mmol). The reaction mixture was stirred at room temperature overnight. After disappearance of the starting material as indicated by TLC, a solution of saturated NH4C1 solution (5 mL) was added dropwise at room temperature. The mixture was then diluted with Et20 (30 mL) and washed three times with water (30 mL), and brine (30 mL). Organic layer was dried over Na2S04, concentrated under vacuum, and the residue was purified by column chromatography to provide compound 223.

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; WANG, Hua; KHANFAR, Mohammad; WO2014/100833; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts