Category: nitriles-buliding-blocks

Electric Literature of 7251-09-4,Some common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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: A mixture of an aldehyde (1.0 eq) and an amine (1.0 eq) was heated in a sealed tube at 60 C for 6 h. The crude material was dried under vacuum over phosphorus(V) oxide to give quantitatively the imine which was used in the next step without further purification.

The synthetic route of 7251-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
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Application of 403-54-3, A common heterocyclic compound, 403-54-3, name is 3-Fluorobenzonitrile, molecular formula is C7H4FN, 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.

A solution of 3-fluorobenzonitrile (70; 20.0 g, 165 mmol) and EtOH (50 m L) and was cooled with an ice-bath. HC1 gas was bubbled through the solution unti l saturation and the reaction mixture was stirred overnight. The solid was col lected by filtration and was washed with cold ether to obtain ethyl-3-fluorobenzimidate hydrochloride as a solid (71 ; 33.5 g, 99% yield). MS (ESI) calcd for C9H,0FNO-HC1: 203.64.

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; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
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52798-01-3, name is Methyl (4-cyanophenyl)acetate, 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 Methyl (4-cyanophenyl)acetate

a) To a solution of methyl (4-cyanophenyl)acetate (4.00 g, 27.8 mmol) in MeOH (20 ml_), hydroxylamine hydrochloride (3.17 g, 45.7 mmol) and NaHCO3 (3.84 g, 45.7 mmol) is added. The suspension is stirred at 600C for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in DCM, washed with water followed by brine, dried over MgSO4, filtered, concentrated and dried to give methyl [4-(N-hydroxycarbamimidoyl)- phenyl]-acetate (3.67 g) as a colourless oil; LC-MS: tR = 0.50 min, [M+1]+ = 209.05.

The synthetic route of 52798-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/29370; (2008); A1;,
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Reference of 119584-73-5, The chemical industry reduces the impact on the environment during synthesis 119584-73-5, name is 2-Ethoxy-6-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 2-ethoxy-6-fluorobenzonitrile (2.00 g, 12.1 mmol, 1 eq) in ethanol (30 mL) was added hydrazine hydrate (0.884 mL, 18.1 mmol, 1.5 eq) at RT. The mixture was heated to 70 C. for 30 h. After cooling to RT, water (20 mL) was added, the mixture was extracted with ethyl acetate (2*50 mL), the combined organic phases were washed with brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo. The residue was triturated with MTBE (10 mL), filtered and the residue was dried for 16 h at 50 C. in vacuo to yield the title compound 4-ethoxy-1H-indazol-3-amine (1.01 g, 47% of theory).

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, 2-Ethoxy-6-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Hassfeld, Jorma; KINZEL, Tom; Koebberling, Johannes; CANCHO GRANDE, Yolanda; BEYER, Kristin; Roehrig, Susanne; Koellnberger, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; US2015/126449; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5724-56-1, name is 2,3-Dimethylbenzonitrile, 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 5724-56-1, Safety of 2,3-Dimethylbenzonitrile

Description 1: 2,3-Bis(bromomethyl)benzonitrile. A mixture of 2,3-dimethylbenzonitrile (available from Fluorochem, 5g, 38.1 mmol), N- bromosuccinimide (13.6g, 76.2mmol) and benzoyl peroxide (460mg, 1.9mmol) in carbon tetrachloride (270ml) was stirred and heated at 800C for 20 hours then cooled and washed with 4x60ml of water. The organic phase was dried (magnesium sulphate), evaporated and purified by flash chromatography eluting with ethyl acetate/iso-hexane (1 :9) to give a yellow solid which was 58% pure by LC/MS. 1H NMR (CDCI3) delta : 4.63 (2H, s), 4.82 (2H, s), 7.43 (1 H, t), 7.64 (2H, m).

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, 2,3-Dimethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80729; (2009); A1;,
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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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-3-fluorophenylacetonitrile

To a solution of compound A26-3 (9.6 g, 45 mmol) in THF (100 ml) under N2 at room temperature was added LDA (2M inTHF, 56 ml) over 1 h. Then the mixture was treated with iodomethane (22. 3g, 157.5 mmol). The mixture was then quenched by adding H20 (50 mL) and extracted with EtOAc (100 mL) three times. The combined organic layers were washed with brine, dried over Na2504, and concentrated in vacuo to provide a residue, which was purified by chromatography over silica gel (eluting with PE: EA=10: 1) to give compound A26-4.

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BIFU, Tesfaye; BIJU, Purakkattle; BLIZZARD, Timothy A.; CHEN, Zhengxia; CLEMENTS, Matthew J.; CUI, Mingxiang; FRIE, Jessica L.; HAGMANN, William K.; HU, Bin; JOSIEN, Hubert; NAIR, Anilkumar G.; PLUMMER, Christopher W.; WO2015/176267; (2015); A1;,
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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 41171-91-9 as follows. Product Details of 41171-91-9

To the solution of 3-cyanocyclopentanone prepared above (91.6 g) in MeOH (1300 ml) was added NaBH4 (32.0 g) in portions while maintaining the temperature between 20- 30 C. After the addition was completed the mixture was stirred at rt for 30min. The mixture was evaporated and purification of the residue by column chromatography on silica gel (50 % petroleum ether/EtOAc) afforded 3-Hydroxy-cyclopentanecarbonitrile (62.0 g) as a colorless oil. T

According to the analysis of related databases, 41171-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BERGERON, Philippe; BODIL VAN NIEL, Monique; DRAGOVICH, Peter; HURLEY, Christopher; KULAGOWSKI, Janusz; LABADIE, Sharada; MCLEAN, Neville James; MENDONCA, Rohan; PULK, Rebecca; ZAK, Mark; WO2013/7765; (2013); A1;,
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Related Products of 51762-67-5, 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. 51762-67-5, name is 3-Nitrophthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(. 3. 18 g, 21 17 mmol), anhydrous potassium carbonate (. 15.20 g, 0 11 mol) was added to the IJ IOOml round-bottomed flask, dissolved in acetonitrile and heated to 90 C under nitrogen; 3- nitro-phthalonitrile (. 1.83 g, 10 58 mmol) dissolved in acetonitrile after transfer to constant pressure dropping funnel and slowly added dropwise to the flask, continued after the addition was complete the reaction at 90 C at 18 h; After completion of the reaction, acetonitrile was removed by rotary evaporation under reduced pressure, the residue was extracted with methylene chloride; the resulting crude product with dichloromethane – methanol 30: 1 (v / v) as eluent, separated by silica gel column chromatography to give a pale after yellow oily liquid Technology Xhttp://www.technology-x.net/A61K/201410486382_2.html

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

Reference:
Patent; Fuzhou University; Liu, Jianyong; Ye, Farong; Lu, Yuan; (24 pag.)CN104311566; (2016); B;,
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Synthetic Route of 859855-53-1, These common heterocyclic compound, 859855-53-1, name is 3-Amino-4-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.

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 Na2CO3 and extracted with DCM (2¡Á200 mL). The organic layers were combined, dried over Na2SO4, 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). 1H NMR (400 MHz, d6-DMSO) delta 10.40 (s, 1H), 9.43 (td, J=1.2, 6.8 Hz, 1H), 8.63 (s, 1H), 8.21 (dd, J=2.0, 7.2 Hz, 1H), 7.78-7.84 (m, 2H), 7.54-7.63 (m, 2H), 7.22 (dt, J=1.2, 6.8, 1H). 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). 1H NMR (400 MHz, d6-DMSO) delta 10.21 (s, 1H), 9.70 (s, 1H), 9.45 (td, J=1.2, 7.2 Hz, 1H), 8.61 (s, 1H), 7.95 (dd, J=2.4, 7.6 Hz, 1H), 7.79 (td, J=1.2, 8.8 Hz, 1H), 7.51-7.60 (m, 2H), 7.31-7.37 (m, 1H), 7.19 (dt, J=1.2, 6.8, 1H), 5.88 (s, 2H). MS m/z 314.1 (M+1)+.

Statistics shows that 3-Amino-4-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 859855-53-1.

Reference:
Patent; IRM LLC; YEH, Vince; LI, Xiaolin; LIU, Xiaodong; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; US2013/59846; (2013); 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. 85068-32-2, name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, A new synthetic method of this compound is introduced below., Safety of 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile

General procedure: Absolute ethyl alcohol (100 mL), substituted benzylcyanide (5.4 mmol), and 2,3,4-trimethoxybenzaldehyde (5.4 mmol) were added to three-necked reaction flask with a mechanical stirrer. The reaction mixture was stirred for 0.5 h at 70 C. Then, a sodium hydroxide (20 %) solution was added dropwise until a precipitate formed. The reaction was cooled to room temperature and the mixture was poured into ice-water. The residue was filtered and washed with hot water to pH 7. The crude product was dried under vacuum and then recrystallized in ethanol

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; Oezen, Furkan; Tekin, Suat; Koran, Kenan; Sandal, Sueleyman; Goerguelue, Ahmet Orhan; Research on Chemical Intermediates; vol. 42; 12; (2016); p. 7793 – 7805;,
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