Реакция #41267

Уравнение реакции

hydroxylamine hydrochloride

HATU

DIPEA

E-3-chloro-4-hydroxyphenylcinnamic acid

→

title compound

Выход 9.7%

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

Выход 9.7%

Растворители

DMF

Условия реакции

Обработка

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

Методика

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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