反应 #1509596

反应方程式

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

溶剂

trimethylorthoacetate

反应条件

后处理

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

实验过程

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).

来源