반응 #1509596

반응 방정식

2-Chloro-N-hydroxy-6-methyl-isonicotinamidine

acetic acid

→

title compound

2-Chloro-6-methyl-4-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyridine

용매

trimethylorthoacetate

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도After cooling to room temperature the solvent
3. 3
   기타was evaporated under reduced pressure
4. 4
   기타the residue partitioned between EtOAc and aqueous solution of NaHCO3
5. 5
   기타The organic layer was separated
6. 6
   세척washed with water and brine
7. 7
   기타dried under Na2SO4
8. 8
   여과filtered
9. 9
   기타the solvent was evaporated under reduced pressure
10. 10
    기타The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 9/1)

실험 절차

2-Chloro-N-hydroxy-6-methyl-isonicotinamidine (120 mg) was suspended in trimethylorthoacetate (3 ml) under inert atmosphere and acetic acid (0.3 ml) was added. The mixture was heated to 100° C. and stirred for 2 h. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue partitioned between EtOAc and aqueous solution of NaHCO3. The organic layer was separated, washed with water and brine, dried under Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 9/1) affording the title compound (107 mg).

출처