تفاعل #157879

معادلة التفاعل

Water

O-cyclopentylhydroxylamine

6-[3-chloro-4-(methylsulfonyl)benzoyl]-3-methylpyridin-2(1H)-one

O-cyclopentylhydroxylamine

→

(E)-6-{[3-chloro-4-(methylsulfonyl)phenyl](cyclopentyloxyimino)methyl}-3-methylpyridin-2(1H)-one

المردود 34.0%

المذيبات

n-butanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred under microwave irradiation at 200° C. for three hours
2. 2
   استخلاصfollowed by extraction with chloroform
3. 3
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىThe solvent was then evaporated under reduced pressure
6. 6
   أخرىThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1)
7. 7
   أخرىfurther purified by silica gel column chromatography (chloroform:ethyl acetate=50:1→25:1)
8. 8
   ترشيحThe resulting less polar product was powdered with an ethyl acetate/hexane solution, and filtration operation

الإجراء التجريبي

O-cyclopentylhydroxylamine (0.3 mL) was added to a solution of 6-[3-chloro-4-(methylsulfonyl)benzoyl]-3-methylpyridin-2(1H)-one (220 mg) in n-butanol (2 mL) at room temperature, and the mixture was stirred under microwave irradiation at 200° C. for two hours. O-cyclopentylhydroxylamine (0.3 mL) was further added at room temperature, and the mixture was stirred under microwave irradiation at 200° C. for three hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1→1:1) and further purified by silica gel column chromatography (chloroform:ethyl acetate=50:1→25:1). The resulting less polar product was powdered with an ethyl acetate/hexane solution, and filtration operation gave (E)-6-{[3-chloro-4-(methylsulfonyl)phenyl](cyclopentyloxyimino)methyl}-3-methylpyridin-2(1H)-one as a white solid (95 mg, 34%). The more polar product was powdered with an ethyl acetate/hexane solution, and filtration operation gave (Z)-6-{[3-chloro-4-(methylsulfonyl)phenyl](cyclopentyloxyimino)methyl}-3-methylpyridin-2(1H)-one as a white solid (36 mg, 13%).

المصدر