反应 #41267

反应方程式

hydroxylamine hydrochloride

HATU

DIPEA

E-3-chloro-4-hydroxyphenylcinnamic acid

→

title compound

收率 9.7%

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

收率 9.7%

溶剂

DMF

反应条件

后处理

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

实验过程

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).

来源