Реакция #1509596

Уравнение реакции

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

Растворители

trimethylorthoacetate

Условия реакции

Обработка

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

Методика

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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