New downstream synthetic route of 4-Cyano-N-methoxy-N-methylbenzamide

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

Adding a certain compound to certain chemical reactions, such as: 116332-64-0, name is 4-Cyano-N-methoxy-N-methylbenzamide, 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 116332-64-0, Quality Control of 4-Cyano-N-methoxy-N-methylbenzamide

To a -780C stirred solution of trimethyl (2-methylbut-3-yn-2-yloxy) silane (3.3 g, 20.00 mmol) in dry THF (45 mL), «-BuLi (4.1 mL, 9.00 mmol, 1.6 M in hexane) was added dropwise over 10 minutes under an inert atmosphere. The reaction mixture was stirred for 30 min at -78 0C, and then a solution of 4-cyano-N-methoxy-N-methylbenzamide (2.0 g, 10.00 mmol) in dry THF (15 mL) was added to the reaction mixture and stirring was continued for an additional 1 h at -78 0C. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried OVCr Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography eluting with 15 % EtOAc in hexanes to afford 4-(4- methyl-4-(trimethylsilyloxy) pent-2-ynoyl) benzonitrile (3.8 g, 68 %) as a yellow oil.

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

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Application of 116332-64-0, The chemical industry reduces the impact on the environment during synthesis 116332-64-0, name is 4-Cyano-N-methoxy-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

A solution of n-butyllithium (2.5 M in hexanes, 0.8 mL, 2.0 mmol) was added dropwise by syringe to a solution of 6-bromo-4-chloro-2-methoxy-3-((4-(trifluoromethyl)piperidin-1-yl)methyl)quinoline (0.964 g, 2.20 mmol, Intermediate 40) in dry deoxygenated THF (14 mL) at -78 C. After 2 minutes, a solution of 4-cyano-N-methoxy-N-methylbenzamide (0.13 g, 0.50 mmol, Intermediate 78: step a) in dry THF (4 mL) was added dropwise by syringe. An additional 2 mL of THF was used to complete the quantitative addition. After 2 hours of stirring at -78 C., the reaction was quenched with saturated aqueous ammonium chloride solution and the mixture was partitioned between water and EtOAc. The layers were separated and the aqueous phase was further extracted with EtOAc and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography to provide the title compound.

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-Cyano-N-methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts