Category: nitriles-buliding-blocks

Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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 2032-34-0, Quality Control of 3,3-Diethoxypropanenitrile

Step 1. l-cyclopropyl-lH-pyrazol-5-amine [0634] A 100-mL round-bottom flask was charged with 3,3-diethoxypropanenitrile (0.600 g, 4.19 mmol), cyclopropylhydrazine di-hydrochloride (0.610 g, 4.21 mmol) and ethanol (20 mL), and the resulting solution stirred for 18 h at 80 C. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10: 1, dichloromethane/methanol) to afford l-cyclopropyl-lH-pyrazol-5-amine (0.206 g, 36% ) as light yellow oil. MS (ESI, pos. ion) m/z 124[M+H]+.

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Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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Reference of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, 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) 3-Bromo-6-fluoro-2-methylbenzonitrile To a cooled (0 C.) solution of 2-fluoro-6-methylbenzonitrile (2 g, 14.8 mmol) in concentrated sulfuric acid (40 mL) was added NBS (2.7 g, 15.6 mmol). The resulting residue was stirred at 0 C. for 3 hrs and poured into ice-water (400 mL). The resulting solution was extracted three times with EtOAc (80 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography to yield 3-bromo-6-fluoro-2-methylbenzonitrile.

The synthetic route of 198633-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Sui, Zhihua; Subasinghe, Nalin; US2014/275172; (2014); 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. Formula: C6H7NO

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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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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 2-cyano-4,4-diethoxybutyrate

2-Methyl-4-hydroxypyrrolo[2,3-d]pyrimidine (3).; Acetamidine hydrochloride (2, 0.05 mol, 4.7 g) was added to the 0.1 M sodium ethoxide solution (75 ml) and kept stirring under room temperature for 0.5 h. After removing the formed sodium chloride by filtration, the filtrate was added the ethyl alpha-cyano-gamma,gamma-diethoxybutyrate (1, 0.05 mol, 11.5 g) and the solution was heated under reflux for 5 h. After the removal of most solvent under vacuum, acetic acid was added to adjust the pH to 7.0 and 10.8 g precipitation as white powder. Ethanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder and was refluxed for 2 h. By the end of the reaction an equal volume of water was added and kept at 4° C. overnight. The pyrrolopyrimidine 3 precipitated as white powder (2.1 g) was used for next step without further purification.

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; Gangjee, Aleem; US2010/10016; (2010); A1;,
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Electric Literature of 3939-09-1, 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. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Benzyl alcohol (0.77 g, 7.2 mmol) was added to a stirred suspension of potassium tert-butoxide (0.97 g, 8.6 mg) in dioxane (15 ml) at room temperature. After 10 minutes of stirring at room temperature 2,4-difiuorobenzonitrile (1.00 g, 7.2 mmol) was added in one portion. After another 90 minutes water (10 ml) was added and the mixture extracted with diethyl ether (3×10 ml), the combined organic phases were dried using a phase separator and concentrated to solids. The crude material was purified by column (0491) chromatography using silicon dioxide gel, eluting with 25-50% dichloromethane in petroleum ether to afford 2-(benzyloxy)-4-fluorobenzonitrile as a white solid (1.33 g, 81%). (0492) [00317] A cold solution of borane (1.4 ml, 1 M in tetrahydrofuran) was added to 2- (benzyloxy)-4-fluorobenzonitrile (208 mg, 915 mutauetaomicron). After 15 hours of stirring at room temperature additional borane (1.4 ml, 1 M in tetrahydrofuran) was added. After another 19 hours of stirring additional borane (1.0 ml, 1 M in tetrahydrofuran) was added. After 3 hours the mixture was added to sodium hydroxide (5 ml, 1 M aqueous), extracted with ethyl acetate (3×5 ml), the combined organic phases were dried using a phase separator and concentrated afford [2-(benzyloxy)-4-fluorophenyl]methanamine as oil (260 mg, quantitative). This material was used without further purification. (0493) [00318] N-Methyl-4-piperidone (150 mg, 1.32 mmol) was added to a stirred solution of [2-(benzyloxy)-4-fluorophenyl]methanamine (204 mg, 882 mueta omicron) in ethanol (5 ml), after 5 minutes sodium triacetoxyborohydride (372 mg, 1.76 mmol) was added. After 6 hours the reaction mixture was concentrated, redissolved in dichloromethane (5 ml), washed with sodium hydroxide (5 ml, 1 M aqueous), the aqueous phase was extracted with additional dichloromethane (2×1 ml), the combined organic phases were dried using a phase separator, and concentrated to afford the desired intermediate as a yellow oil (253 mg, 87 %).

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

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
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Reference of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, 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.

CH3Se3CH3 (100 mg, 0.53 mmol, Aldrich) was added to a solution of NaBH4 (60 mg, 1.59 mmol) in 5 ml of absolute EtOH under N2. After 5 min of vigorous reaction the colour of the solution changed from yellow to white. 5-Bromopentanenitrile (0.17 g, 1.06 mmol, Acros) was then added and stirred for 2.5 h. Et2O (10 ml) was added, the reaction mixture was washed with 5 ml each of water and brine, extracted with 2 x 25 ml of Et2O, and dried (MgSO4). The solvent was removed to give 10b as a yellow oil (107 mg, 57% yield). EI-ToF-MS (Fig. 2), m/z (rel. int.): 177 [M]+ (1200), 175 (28), 173 (15), 135 (10), 109 [CH3SeCH2]+ (33), 107 (17), 96 [CH3SeH]+ (27), 94 [CH2Se]+ (21), 93 [CHSe]+ (25), 82 (22), 55 (4). 1H NMR (500 MHz, CDCl3): delta1.75-1.88 (m, 4H, CH2CH2), 2.00 (s, 3H, CH3Se), 2.38 (t, 2H, J = 6.8 Hz, CH2CN), 2.57 (t, 2H, J = 6.9 Hz, CH2Se).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matich, Adam J.; McKenzie, Marian J.; Lill, Ross E.; Brummell, David A.; McGhie, Tony K.; Chen, Ronan K.-Y.; Rowan, Daryl D.; Phytochemistry; vol. 75; (2012); p. 140 – 152;,
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Electric Literature of 32446-66-5, The chemical industry reduces the impact on the environment during synthesis 32446-66-5, name is 4,4′-Dicyanobenzophenone, I believe this compound will play a more active role in future production and life.

EXAMPLE 2; PREPARATION OF 4,4′-(HYDROXY METHYLENE)BISBENZONITRILE OF FORMULA IV 200 ml of methanol was taken into a round bottom flask followed by charging 40 g of 4,4-dicyanobenzophenone and stirring for about 10 minutes. 3.28 g of sodium borohydride was added slowly to the above suspension at 0-5 C. followed by stirring at 25-30 C. for 30 minutes, and the formed solution was neutralized with 25 ml of glacial acetic acid to a pH of 6.33. 800 ml of water was charged to the above-neutralized suspension and stirred for 30 minutes, and the precipitate was filtered, washed with 400 ml of water and finally subjected to drying at 55-60 C. under vacuum for 4 hours to afford 40 g of title compound having a purity by HPLC of 99.36% and a water content by the Karl Fischer method of 0.27%.

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, 4,4′-Dicyanobenzophenone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Palle, Venkata Raghavendra Acharyulu; Kalaria, Ashok Jerambhai; Shelke, Sandip Ashok; US2007/100149; (2007); A1;,
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Electric Literature of 1885-38-7, 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. 1885-38-7, name is (E)-Cinnamonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(b) (2E)-3-Phenyl-2-propenimidamide; Cinnanionitrile (25.0 g, 194 mmol) was dissolved in EtOH. The solution was cooled to 0 0C and HCl gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 1 h and then concentrated under vacuum. The residue was dissolved in EtOH (100 niL), cooled to 00C and a solution of NH3/Me0H (7M, 69 mL, 484 mmol) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and stirred overnight and the resulting NH4Cl was filtered off. The solution was concentrated under vacuum and the resulting product was used without further purification (28.6 g crude). LC-MS: m/z 147.4 (MH+).

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, (E)-Cinnamonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); A1;,
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Related Products of 1528-41-2, 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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 1.0 g of 3,3-dimethylcyclohexanone (S6; 7.9 mmol), hydroxylamine hydrochloride (0.66 g,9.5 mmol), 10 mL of ethanol, and 1.6 g of K2CO3 (12 mmol) was heated to 70 C for 64 hours. Themixture was concentrated suspended in 10 mL of water, the extracted three times each with 30 mL ofEtOAc. The extracts were combined and concentrated to provide 1.2 g of 3,3-dimethylcyclohexanoneoxime (S7) that was used crude. To a 0 C solution of S7 (0.20 g, 1.4 mmol) in 2 mL of THF was added dropwise 1.6 M BuLi in hexanes(1.8 mL, 2.8 mmol). The mixture stirred for 30 minutes at room temperature, then ethyl 2-(4-cyanophenyl)acetate (0.27 g, 1.4 mmol) was added. After stirring for 1 hour, 0.7 mL of concentratedH2SO4 was added. After stirring for 1 hour, 25 mL of water was added and the mixture was extractedthree times each with 15 mL of EtOAc. The extracts were concentrated and the residue was purified firstby silica chromatography (0-50% EtOAc in heptanes), then by preparative HPLC (C18 column 10-90%MeCN in H2O, both 0.1% v/v formic acid) or give 41 mg of 16.

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, Ethyl 2-(4-cyanophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meyers, Kenneth; Cogan, Derek A.; Burke, Jennifer; Arenas, Raquel; Balestra, Michael; Brown, Nicholas F.; Chen, Zhidong; Cerny, Matthew A.; Clifford, Holly E.; Colombo, Federico; Fader, Lee; Frederick, Kosea S.; Guo, Xin; Goldberg, Daniel; Hornberger, Keith R.; Kugler, Stanley; Lord, John; Marshall, Daniel R.; Moss, Neil; Parmentier, Jean-Huges; Richman, Jeremy R.; Schmenk, Jennifer; Weldon, Steven M.; Yu, Maolin; Zhang, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 979 – 984;,
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