반응 #41267

반응 방정식

hydroxylamine hydrochloride

HATU

DIPEA

E-3-chloro-4-hydroxyphenylcinnamic acid

→

title compound

수율 9.7%

E-3-[3′-chloro-4′-hydroxybiphenyl-4-yl]-N-hydroxy-acrylamide

수율 9.7%

용매

DMF

반응 조건

후처리

1. 1
   기타the solution thus obtained
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 2 days
3. 3
   기타DMF was removed under reduced pressure
4. 4
   세척the residue was washed with water
5. 5
   기타to obtain
6. 6
   여과after filtration, 140 mg of a crude product
7. 7
   기타Purification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK)
8. 8
   기타water/methanol 1:1 and crystallization from diethyl ether

실험 절차

205 mg (0.75 mmol) of E-3-chloro-4-hydroxyphenylcinnamic acid were dissolved under nitrogen in 7.5 ml of DMF, then 285 mg (0.75 mmol) of HATU and 97 μL (0.56 mmol) of DIPEA were added and the solution thus obtained was kept under stirring at room temperature for 2 min. After addition of hydroxylamine hydrochloride (261 mg, 3.75 mmol), the mixture was stirred at room temperature for 2 days. DMF was removed under reduced pressure and the residue was washed with water to obtain, after filtration, 140 mg of a crude product. Purification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK) using as eluent water/methanol 1:1 and crystallization from diethyl ether afforded 21 mg of the title compound as a white solid. M.p. 172-175° C. Rf=0.16 (RP18 MERCK, H2O/MeOH 1:1).

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