تفاعل #1509596

معادلة التفاعل

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

المذيبات

trimethylorthoacetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر