反応 #1509596

反応方程式

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

溶媒

trimethylorthoacetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度After cooling to room temperature the solvent
3. 3
   その他was evaporated under reduced pressure
4. 4
   その他the residue partitioned between EtOAc and aqueous solution of NaHCO3
5. 5
   その他The organic layer was separated
6. 6
   洗浄washed with water and brine
7. 7
   その他dried under Na2SO4
8. 8
   ろ過filtered
9. 9
   その他the solvent was evaporated under reduced pressure
10. 10
    その他The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 9/1)

実験手順

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).

出典