Hydrazinecarboxaldehyde → 5-Ethenylpyridine-2-carbonitrile

A 5-vinylpicolinonitrile intermediate (1-2) was prepared by adding 5-bromopicolinonitrile (1-1), tetrakis(triphenylphosphine) (Pd(PPH3)4), and 2,6-di-t-butyl-4-methylphenol (BHT) in toluene, adding tributyl(vinyl)stannane thereto, and reacting the resulting mixture at 80° C. for 24 hours. The intermediate (1-2) was added to a methanol solution, in which sodium metal was dissolved, and reacted at 70° C. for 3 hours and then cooled. Formohydrazide (1-3) was added to the reaction solution and reacted at 70° C. for 15 minutes. Then, the temperature was lowered to 25° C. and the reaction solution was reacted for 24 hours until yellow crystals were formed. Upon completion of the reaction, the yellow crystals were collected by filtration, and 2-(4H-1,2,4-triazol-3-yl)-5-vinylpyridine (1-4) was purified by column chromatography using chloroform and methanol as solvents.

1. customat 80° C.
2. customfor 24 hours
3. dissolutionwas dissolved
4. customreacted at 70° C. for 3 hours
5. temperaturecooled
6. customreacted at 70° C. for 15 minutes
7. customwas lowered to 25° C.
8. customthe reaction solution was reacted for 24 hours until yellow crystals
9. customwere formed
10. customUpon completion of the reaction
11. filtrationthe yellow crystals were collected by filtration, and 2-(4H-1,2,4-triazol-3-yl)-5-vinylpyridine (1-4)
12. customwas purified by column chromatography

ORD record

ord-6b1218cab4eb408d9362681a06c4bb38

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150601B2