Reacción #1509596

Ecuación de reacción

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

Disolventes

trimethylorthoacetate

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente