Tag: M.W=100-200

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

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

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

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

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

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

Related Products of 191014-55-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 191014-55-8 name is 4-Fluoro-2-methoxybenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of (S)-3-(l-aminoethyl)-6-chloroquinolin-2(lH)-one hydrochloride II-l (201 mg, 0.776 mmol) and 4-fluoro-2-methoxybenzonitrile (236 mg, 1.56 mmol) in DMSO (5 ml) was treated with DIEA (400 mu, 2.29 mmol) and stirred at 110 C for three days. The sample was diluted with water (75 mL) and extracted with DCM (2×50 mL), dried, and filtered. Silica gel was added, and the solvent was evaporated under reduced pressure. The material was chromatographed by Biotage MPLC (silica gel, 0 to 70% EtOAc in hexanes, with isocratic elution when peaks came off) to provide a gum. The material was dissolved in DCM (10 mL), washed with water (2×10 mL), dried (Na2S04), filtered, and evaporated to provide 76 mg yellow powder. The sample was mixed with MeCN (4 mL) and water (2 mL), frozen on a dry ice/acetone bath, and lyopholyzed to provide the title compound 1-2 (71.1 mg, 0.193 mmol, 24.93 % yield, HPLC purity 96.3% at 220 nm) as a solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 12.07 (s, 1 H), 7.77 (d, J=2.35 Hz, 1 H), 7.74 (s, 1 H), 7.50 (dd, J=8.65, 1.91 Hz, 1 H), 7.35 – 7.20 (m, 3 H), 6.27 (s, 1 H), 6.06 (d, J=7.90 Hz, 1 H), 4.79 – 4.65 (m, 1 H), 3.75 (s, 3 H), 1.43 (d, J=6.45 Hz, 3 H). LCMS (Method 1): Rt 2.37 min., m/z 354.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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. Recommanded Product: 175596-01-7

Step (ii) Raney nickel (2.0 g) was added to a solution of methyl 4-cyano-2-fluorobenzoate (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 ml.) and water (100 niL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3 chi 300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2- 11 uoro-4-( hydroxy meth) l)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; WO2015/25164; (2015); 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. 58949-75-0, name is 4-(2-Oxopropyl)benzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

EXAMPLE 47 2-[(Aminocarbonyl)amino]-4-methyl-5-(4-cyanophenyl)-3-thiophenecarboxamide Prepared by the method of Example 26 from (4-cyanophenyl)acetone. MS (ES) 299 (M-H)-.

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; Baxter, Andrew; Brough, Stephen; Faull, Alan; Johnstone, Craig; McInally, Thomas; US2002/107252; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 354814-19-0,Some common heterocyclic compound, 354814-19-0, name is 5-Amino-2-(trifluoromethyl)benzonitrile, molecular formula is C8H5F3N2, 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.

Intermediate 38: 2-{[3-Cyano-4-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate; Triethylamine (1.09 g, 10.8 mmol) was added to a stirred solution of 5-amino-2- (trifluoromethyl)benzonitrile (Intermediate 37, 1.0 g, 5.37 mmol) in DCM (40 mL), at 0C, and the mixture was stirred for 15 min. Chloro-2-oxoethyl acetate (1.10 g, 8.06 mmol) was added at 0C and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with DCM and washed with ice water, and saturated brine solution. The organic layer was dried over anhydrous Na2S04, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40% EtOAc/pet. ether to give the title compound (1.1 g).MS ES+ve m/z 285 (M-H).1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H), 4.76 (s, 2 H), 7.72-7.82 (m, 1 H), 7.90-8.00 (m, 1 H), 8.08-8.18 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; BESWICK, Paul John; GLEAVE, Robert James; HACHISU, Shuji; VILE, Sadie; BERTHELEME, Nicolas; WARD, Simon E; WO2012/4604; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts