Month: April 2021

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 1483-55-2 as follows. Recommanded Product: 2-Bromo-5-(trifluoromethyl)benzonitrile

To a solution of 2-bromo-5-(trifluoromethyl)benzonitrile (10.0 g, 40 mmol) in dichloromethane (100 mL) was dropwise added a 1.0 M solution of diisobutylaluminum hydride in hexane (48 mL). The resulting solution was stirred under nitrogen at ambient temperature for 1 h and was then diluted by addition of ether (100 mL). After cooling in an ice bath, a 3 N solution of HCl was carefully added, and the mixture was vigorously stirred at ambient temperature for 15 min. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting oil was purified by flash chromatography (5% EtOAc/hexane) affording 5 g of 2-bromo-5-trifluoromethylbenzaldehyde. 1H NMR (CDCl3) delta 10.39 (s, 1H), 8.18 (d, J=2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.70 (dd, J=8.5 Hz, 2 Hz, 1H).

According to the analysis of related databases, 1483-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
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10496-75-0, name is 2-Methoxy-5-nitrobenzonitrile, 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 2-Methoxy-5-nitrobenzonitrile

The 2-methoxy-5-nitrobenzyl cyanide (1eq, 220mg, 1.23mmo1), 20mL of methanol, 10mg of palladium on carbon (10% of mass) were added sequentially in to the 100mL round bottom flask, the bottle connected to the three links, reaction was stirred at room temperature. Vacuum pumping then recharging N2 , repeat this cycle for 3 times , and N2 loading time not less than 5 min. the reaction was allow to react for 30min at room temperature under H2 protection. After the reaction was complete in 30mins , the palladium-carbon was filtered, concentrated, and column chromatography separation (PE: EA = 5: 1) to give 150 mg of product as a white crystalline solid (compound 7). Yield 82%.

The synthetic route of 10496-75-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
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Reference of 198633-76-0, 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. 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Fluoro-6-methyl- benzonitrile (1000 mg, 7.4 mmol) was added to trifluoromethanesulfonic acid (4.98 mL, 56.2 mmol) cooled in ice. The resulting cold solution was treated with N-bromosuccinimide (1380 mg, 7.8 mmol). The mixture was allowed to stir at ambient temperature. After 30 min, the reaction mixture was poured into ice water and extracted with 2 portions dichloromethane. The combined dichloromethane layers were washed with brine, dried over MgS04, filtered, and evaporated to yield 3-bromo-6-fluoro-2-methyl-benzonitrile (1560 mg, 7.3 mmol, 98% yield) as a light brown oil that solidified.

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-Fluoro-6-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; WO2015/35223; (2015); 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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methyl-3-oxopentanenitrile

EXAMPLE 58 Preparation of 1-methyl-3-(1-methylethyl)-5(1H)-pyrazolamine 4-Methyl-3-oxo-pentanenitrile (39.58 g; 0,356 mol) dissolved in glacial acetic acid (400 ml) and methylhydrazine (18.05 g; 0.382 mol) is added thereto, at 15-20 C. The reaction mixture is heated to 70-75 C. under nitrogen stream for about 5 hours. Then the mixture is cooled, and the solvent is evaporated under reduced pressure. The residue is taken up with water (200 ml) and the pH adjusted to about 9. After extraction with methylene chloride, the solvent of the dried organic layer is stripped off. The residue is taken up in ethyl ether and recovered by filtration. M.p. 115-118 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; Gruppo Lepetit S.p.A.; US4954508; (1990); A;,
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Electric Literature of 159847-81-1, 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 159847-81-1 as follows.

A mixture [OF 4- [ (5-chloro-2, 3-dihydro-1H-indol-1-yl) sulfonyl)] benzoic acid. (0.50 g, 1.49 mmol) and oxalyl chloride (5 mL) in CH2C12 (3mL) was treated with DMF (3 [, L)] and heated to [40 C. AFTER] 2h, the mixture was cooed and concentrated in vacuo to give a yellow semi-solid residue that was dissolved in CH2C12 (2 mL) and pipetted into a mixture of methyl [2-amino-5-cyanoBENZOATE] (0.25 g, 1.40 mmol) in pyridine (5 mL) at [5 C.] The mixture was allowed to stir at room temperature overnight and then concentrated in vacuo. The residue was dissolved in [CH2C12] and aqueous IN CHl.The phases were separated. The organic phase was washed with aqueous 1 N HCl, and H2O, dried [(NA2S04),] and concentrated in vacuo to provide a tan solid that was digested in hot ethanol. The cooled mixture was filtered. The solid was dried in a vacuum oven at [60 C] to give 0.42 g (61 %) of cream solid [PRODUCT. 1H] NMR (400 MHz, DMSO-d6) 8 2.95 (t, 2 H), 3.88 (s, 3 H), 4.01 (t, 2 H), 7.26 [(M,] 2 H), 7.49 (d, [1] H), 8. 12 [(M,] 5 H), 8.37 (s, 1 H), 8.53 (d, [1] H), 11.5 (s, 1 H); MS (ESI-) for [C24HL8CLN305S] [M/Z] 493.9 (M-H)-.

According to the analysis of related databases, 159847-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18461; (2004); A2;,
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Synthetic Route of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 41 5-(3-Chloropropyl)Tetrazole A mixture of 3.5 g of 4-chlorobutyronitrile, 2.3 g of sodium azide and 1.9 g of ammonium chloride in 50 ml of dimethylformamide is stirred at 140 C. for 20 hours. The reaction mixture is poured onto ice, basified with 1N sodium hydroxide and extracted twice with ethyl acetate. The aqueous fraction is acidified with acetic acid and extracted with ethylacetate. Evaporation of the ethyl acetate gives 5-(3-chloropropyl)tetrazole which is used directly in the next step.

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-Chlorobutyronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer Pharmaceuticals Inc.; US5051427; (1991); A;,
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Application of 2941-29-9,Some common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, 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 PI 03 2-(pyridin-2-yl)-2,4,5.6-tetrahydrocvclopenta[c1pyrazol-3-amine [00485] Step A: Preparation of 2-(2-(pyridin-2-yl)hvdrazono)cyclopentane- carbonitrile: A solution of 2-hydrazinylpyridine (0.200 g, 1.83 mmol) and 2- oxocyclopentanecarbonitrile (0.200 g, 1.83 mmol) in MeOH (9.16 mL) was treated with concentrated HCl (0.764 mL, 9.16 mmol) and refluxed for 16 hours. The reaction mixture was concentrated in vacuo, and then partitioned in water and DCM. After phase-separation, the aqueous layer was washed with DCM, basified (saturated NaHC03, pH 10), and extracted with DCM. The combined organic layers were dried with MgS04, filtered and concentrated. The crude material was purified by silica column chromatography, eluting with 100percent EtOAc to afford the product (0.289 g, 78.6percent yield). MS (apci) m/z = 201.2 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cyclopentanone-2-carbonitrile, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara J.; CONDROSKI, Kevin Ronald; HUANG, Lily; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78408; (2014); A1;,
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Synthetic Route of 79463-77-7, These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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.

Diphenyl N-cyanocarbonimidate [79463-77-7] (200 mg, 0.81 mmol, 97 mass%) and 4- aminomorpholine [4319-49-7] (100 mg, 0.98 mmol) were dissolved in DCM (2 mL) and 2-propanol (1.57 g, 26.1 mmol) and DIPEA (159 mg, 1.22 mmol) were added. The reaction mixture was stirred at r.t. for ~1 h before concentrating in vacuo. The crude residue was purified by flash column chromatography on silica (gradient elution with 15-100% EtOAc/hexane) to afford the title compound (170 mg, 85%) as a white solid. dH (300 MHz, DMSO -d6) 10.39 (s, 1H), 7.42 (t, J 7.8 Hz, 2H), 7.28 (t, J 7.4 Hz, 1H), 7.23 – 7.08 (m, 2H), 3.68 (s, 4H), 2.89 (s, 4H). INTERMEDIATES 222 and 223

Statistics shows that Diphenyl N-cyanocarbonimidate is playing an increasingly important role. we look forward to future research findings about 79463-77-7.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); 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. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C12H11NO

To a stirred solution of 1 (0.8 g, 4.3 mmol), NMO (2.9 g, 21.6 mmol) and (S,S)-Jacobsen catalyst (0.06 g, 0.10 mmol) in CH2Cl2 (30 mL) was added m-CPBA (1.5 g, 8.6 mmol) over 30 min at 0 C under N2 atmosphere. The resulting mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et2O (50 mL), and quenched with 5% H2SO4 in H2O (7.5 mL). The aqueous phase was extracted with EtOAc (30 mL x 3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc = 6:1) to afford 11 0.82g (4.1 mmol, 94%) as white solid. Rf = 0.60 (n-hexane/EtOAc = 3:1); mp = 142-144 oC; [alpha]D25 = -97.9 (c 0.1, MeOH); IR (neat) nu 2980, 2226, 1615, 1579, 1490, 1466, 1371, 1347, 1279, 1238, 1209, 1155, 1131, 1106, 1045, 955, 911, 866, 808 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J = 2.0 Hz, 1H), 7.53 (dd, J = 8.5, 2.0 Hz, 1H), 6.87 (d, J = 8.5 Hz, 1H), 3.92 (d, J = 4.3 Hz, 1H), 3.54 (d, J = 4.4 Hz, 1H), 1.60 (s, 3H), 1.30 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 156.5, 134.4, 133.8, 121.1, 119.0, 118.7, 104.3, 74.6, 62.3, 49.9, 25.5, 23.0; HRMS (ESI) calcd for C12H12NO2 [M+H]+ 202.0867, found 202.0861; HPLC (Daicel OD-RH column, n-Hexane:Isopropylalcohol = 95:5, 0.5 ml/min, 254nm) Rt (major) = 18.19 min, Rt (minor) = 20.00; ee = 91%.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Sang-Ho; Kim, Yeon Su; Jung, Jun Min; Boggu, Pulla Reddy; Kim, Seung Chan; Kim, In Su; Jung, Young Hoon; Tetrahedron Letters; vol. 61; 5; (2020);,
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Reference of 1247885-40-0, These common heterocyclic compound, 1247885-40-0, name is 2,3-Difluoro-5-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.

A solution of 2,3-difluoro-5-nitrobenzonitrile (35 mg, 0.19 mmol) in acetonitrile (2 mL) was cooled to 00C. Acetic acid (228 mg, 3.80 mmol) and iron filings (75 mg, 1.33 mmol) were added, and the mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the filtrate was concentrated to give the crude product which was purified by prep-TLC (PE : EA = 2 : 1) to give the title compound as a yellow solid. (14 mg, 48%); LC/MS: m/e = 155 (M+H)+.

Statistics shows that 2,3-Difluoro-5-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 1247885-40-0.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
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