Réaction #1509596

Équation de réaction

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

Solvants

trimethylorthoacetate

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source