Reaction #41267

Reaction equation

hydroxylamine hydrochloride

HATU

DIPEA

E-3-chloro-4-hydroxyphenylcinnamic acid

→

title compound

Yield 9.7%

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

Yield 9.7%

Solvents

DMF

Conditions

Workup

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

Procedure

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).

Source