Preparation and application of 4-methoxypyridine_Industrial additives

Background and overview of preparation and application of 4-methoxypyridine

4-Methoxypyridine is a pyridine derivative. Pyridine and its derivatives are not only the most important components in pesticides, drugs and materials science, but also very important organic synthesis intermediates.

Preparation and application of 4-methoxypyridine

Dissolve (50mmo1) 4-methoxypyridine-N-oxide in 50mL acetonitrile solution at room temperature, and then add 1.01g (55mmo1) cyanuric chloride (TCT) into the reaction solution in batches , TCL tracks the reaction. After the reaction is completed, add 20 mL of saturated sodium carbonate solution dropwise to the reaction solution and stir for 30 min. Dichloromethane was added for extraction, the organic phase was washed with water and saturated brine, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by column to obtain the target product. Light yellow oily liquid. ^{Pyridinemethylamine 1}HNMR (MHz, CDCl₃), 6: 3.83 (s, 3H); 6.80 (d, 2H, J=6Hz); 8.42 (d, 2H, J=6Hz).

Preparation and application of 4-methoxypyridine

CN201310186804.0 discloses a synthesis method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone, step 1, 1-Cbz-2-methyl-3,4-dihydro- Synthesis of 4-piperidone, step 2. Synthesis of 1-Cbz-2-methyl-4-piperidone ferrocenylborate, step 3. 1-tert-butoxycarbonyl-2-methyl-4-piperidone Synthesis of ketinone. The present invention uses 4-methoxypyridine as raw material, first reacts with Cbz-Cl at low temperature, then adds with methylmagnesium chloride, uses zinc powder to reduce, and hydrogenates. The entire route is easier to scale up than the existing technology for production. It is more suitable for industrial large-scale production, has low energy consumption and greatly improves the yield.

References

[1] Liu Yali, Fei Hongyan, Jin Xinhua, Zhang Yunhui. Research on the method of reducing pyridine-N-oxide derivatives to pyridine derivatives by cyanuric chloride (TCT) [J]. Chemical Reagents, 2013, 35 (12):1077-1078+1142.

[2]CN201310186804.0 A kind of synthesis method of 1-tert-butoxycarbonyl-2-methyl-4-piperidone