Reaktion #1509596

Reaktionsgleichung

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

Lösungsmittel

trimethylorthoacetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

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