Month: May 2021

Application of 1114546-30-3, These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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.

Reference Example 3 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile To a solution of 4-bromo-2-fluoro-3-methylbenzonitrile (1.10 g), (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (1.18 g), cesium carbonate (2.51 g), tris(dibenzylideneacetone)dipalladium(0) (235 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (297 mg) in dioxane (30 mL) was stirred under an argon atmosphere at 80 C. for 8 hr. 5 The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (yield: 347 mg, 19%). 1H-NMR(CDCl3)delta:0.11(6H,d,J=7.2 Hz), 0.91(9H,s), 1.04(3H,d,J=6.4 Hz), 2.19(3H,d,J=2.3 Hz), 2.50(1H,dd,J=16.8,2.4 Hz), 2.78(1H,dd,J=16.8,5.4 Hz), 4.09-4.22(1H,m), 4.44-4.50(1H,m), 6.96(1H,d,J=8.7 Hz), 7.45-7.53(1H,m).

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 69797-49-5, The chemical industry reduces the impact on the environment during synthesis 69797-49-5, name is 2-Amino-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 2-amino-3- methylbenzonitrile (0.85 g, 6.4 mmol) in THF (17 ml) was added triethylamine (0.99 ml, 7.1 mmol) followed by phosgene (20 % in toluene, 3.41 ml, 6.4 mmol). The RM was heated at reflux for 4 h then allowed to cool to RT. The THF was evaporated in vacuo and the residue precipitated with cold pentane. The resulting mixture was filtered and the filtrate evaporated to give the title compound as a yellow oil. Y = 74 %. MS ES+: 232.0 (compound analysed in diethylamine to generate diethyl urea).

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-Amino-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 51632-12-3, name is 2-(4-Bromophenyl)-3-methylbutanenitrile, A new synthetic method of this compound is introduced below., Formula: C11H12BrN

SYNTHESIS EXAMPLE 2 4-Bromo-alpha-isopropyl-phenylacetic acid 20 g of 4-bromo-alpha-isopropylphenylacetonitrile was heated with 140 ml of sulfuric acid (50V/V%) at 145 C for 6 hours. The cooled reaction mixture was poured onto 150 g of ice, and extracted with ether (100 ml * 3). The ether layers were combined and extracted with three 70 ml portions of cold 5% sodium hydroxide solution, and the aqueous extracts were acidified with concentrated hydrochloric acid, and then extracted with ether. The ether extract was washed successively with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate. Removal of the solvent gave 16.9 g (78.2%) of white crystals, which were sufficiently pure for use in next step. A portion of the crystals was recrystallized from benzene, melting point: 97 – 98 C.

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; Sumitomo Chemical Company, Limited; US3996244; (1976); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 97582-88-2, name is 3-(Difluoromethoxy)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 97582-88-2, Safety of 3-(Difluoromethoxy)benzonitrile

(1) A Grignard reagent prepared by using 0.75 g of magnesium, 4.46 g of 2-bromopropane and 24 ml of anhydrous diethyl ether, was dropwise added to a mixture comprising 4.09 g of 3-difluoromethoxybenzonitrile and 20 ml of anhydrous diethyl ether. After completion of the dropwise addition, the mixture was reacted at room temperature for 27 hours. The reaction mixture was put into ice water, and 6N sulfuric acid was added to bring the mixture to be weakly acidic, followed by stirring for 0.5 hour. The mixture was extracted with diethyl ether and washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=l/19), to obtain 2.04 g of 3-difluoromethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.XH-NMR 5ppm (Solvent: CDCl3/300 MHz)1.23(d,6H),3.52(m,lH),6.56(t,lH),7.32(dd,lH),7.48(t, 1H),7.70(s,lH),7.80(d,lH)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 61272-77-3, name is 2-Amino-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 61272-77-3

Synthesis Example 13 1-benzyl-6-fluoro-2,3-dihydro-1H-pyrrolo [2,3-b] quinoline-4-ylamine hydrochloride Phosphorus oxychloride (0.51 ml) was added to a solution of 1-benzyl-2-pyrrolidone (0.84 ml) in chloroform (3 ml). The solution was stirred at room temperature for 30 minutes, and 2-amino-5-fluorobenzonitrile (0.65 ml) was added thereto. The reaction mixture was refluxed for 3 hours while heating and then ice-water was added thereto. Further, the mixture was neutralized by adding 20% aqueous sodium hydroxide solution and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene) amino} benzonitrile (1.68 g).

According to the analysis of related databases, 61272-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tarui, Naoki; Santo, Takashi; Mori, Masaaki; Watanabe, Hiroyuki; US2003/139442; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 69797-49-5,Some common heterocyclic compound, 69797-49-5, name is 2-Amino-3-methylbenzonitrile, molecular formula is C8H8N2, 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.

b. 2-[1-Oxo-5-(2-propenyl)-2-cyclopenten-3-yl]amino3-pentylbenzonitrile (Formula II, A=formula Ia, X=>C-H, n=1, Ra=pentyl, Rb=2-propenyl) A procedure similar to that described in Example 11b was followed using the following changes and substitutions: 2-amino-3-pentylbenzonitrile (1.51 g) from Example 10e instead of the nitrile from Example 1d, and 4-(2-propenyl)-1,3-cyclopentanedione (1.30 g instead of the amount indicated in Example 11b) in toluene (10 ml instead of the amount indicated in Example 11b). Following a heating interval of 5.5 hours, excess toluene was distilled off and the residue cooled to ambient temperature. Partitioning of the residue between saturated aqueous NaHCO3 and ethyl acetate was followed by separation of the layers and washing of the ethyl acetate layer with brine. After drying and concentrating the material, the crude product was chromatographed over silica gel using ethyl acetate:hexane (1:1) as the eluent. There was obtained the title product (1.21 g, 49%) as a yellow gum; tlc, Rf =0.23, silica gel, ethyl acetate:hexane (1:1).

The synthetic route of 69797-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICI Americas Inc.; US4975435; (1990); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1885-29-6, name is 2-Aminobenzonitrile, 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 1885-29-6, Quality Control of 2-Aminobenzonitrile

Bromine (110 mmol, 5.6 mL) was added dropwise to an acetic acid solution (150 mL) of 2-aminobenzonitrile (50 mmol, 5.9 g) in an argon atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice water (200 mL), and the resulting solid was collected by filtration and washed with water.The residue was recrystallized from ethyl acetate to obtain 2-amino-3,5-dibromobenzonitrile (6.9 g, yield 50%).The obtained 2-amino-3,5-dibromobenzonitrile (10.0 mmol, 2.75 g), tetrabutylammonium fluoride trihydrate (5.0 mmol, 1.58 g), trimethylsilyl azide (TMSN3) (15 0.0 mmol, 2.0 mL) was stirred at 85 C. for 2 hours under an argon atmosphere. Ethyl acetate was added to the reaction solution, and the mixture was extracted 3 times with 1M hydrochloric acid (5 mL), and then the organic layer was dried over magnesium sulfate and dried under reduced pressure.Ethyl acetate was distilled off. The residue was subjected to silica gel column chromatography (ethyl acetate: ethanol = 10: 1), and 2,4-dibromo-6- (1H-tetrazol-5-yl) aniline (1.40 g, yield 44%) was white. Obtained as a solid.

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

Reference:
Patent; Tohoku University; Uozumi, Nobuyuki; Arisawa, Mieko; Suzuki, Futoshi; Endo, Akira; Hamamoto, Susumu; Ikenokami, Yoshiaki; (20 pag.)JP2019/137678; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 320-41-2, name is 4-Chloro-2-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H3ClF3N

Add 4-chloro-2-trifluoromethyl-benzonitrile to formic acid (96percent) (15 mL) and water (3 mL). Add nickel-aluminun alloy (1260 mg). Heat at 100 0C overnight. Dilute with ethyl acetate and filter through Celite.(R).. Extract the filtrate with 1 N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 4-chloro-2-trifluoromethylbenzaldehyde (555 mg, 87percent): 1HNMR (400 MHz, MeOH-d4) delta 10.29 (m, IH), 8.10 (d, IH, J = 8.4 Hz), 7.91 (d, IH, J = 1.6 Hz)5 7.85 (dd, IH, J = 8.4, 1.6 Hz).

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; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 453566-15-9, name is Methyl 3-bromo-5-cyanobenzoate, 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. category: nitriles-buliding-blocks

To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 %). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 %).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) delta 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).

The synthetic route of Methyl 3-bromo-5-cyanobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 69975-66-2, name is 3-Oxo-indan-5-carbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C10H7NO

[00286] To a solution of 3-oxo-2,3-dihydro-lH-indene-5-carbonitrile (200 mg, 1.27 mmol) in acetic acid (6 mL) was added nicotinaldehyde (0.14 g, 1.27 mmol), ethyl 2-cyanoacetate (0.2 g, 1.78 mmol) and ammonium acetate (0.98 g, 12.7 mmol). The reaction mixture was heated to 80 C and stirred at that temperature for 10 min under microwave irradiation. Then the reaction mixture was cooled to RT. Water (20 mL) was added to the reaction vessel, which resulted in the formation of a precipitate. The precipitate was filtered, washed with water (3 x 5 mL), ether (3 x 5 mL) and then purified by flash column chromatography with a gradient elution of EtOAc (30%) and Hex (70%) to EtOAc (70%) and Hex (30%) to provide 2-oxo-4-(pyridin-3-yl)-2,5- dihydro-lH-indeno[l,2-b]pyridine-3,8-dicarbonitrile (20 mg, 0.06 mmol) as a yellow solid. LC/MS [M+H]+ = 311.3.

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; SUNOVION PHARMACEUTICALS INC.; NEWCOM, Jason, S.; SPEAR, Kerry, L.; WO2015/88564; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts