Diisopropylethylamine → E-3-[4'-hydroxybiphenyl-3-yl]-N-hydroxyacrylamide

Participants

Reaction Conditions

Reaction Steps

70 mg (0.29 mmol) of E-3-(4′-hydroxybiphenyl-3-yl)-acrylic acid were dissolved under nitrogen in 3 ml of DMF, then 109 mg (0.29 mmol) of HBTU and 100 μL (0.57 mmol) of DIPEA were added at 0° C. After 5 min hydroxylamine hydrochloride (20 mg, 0.29 mmol) was added and the mixture was stirred at 0° C. for 10 min., then at room temperature for 4 h. DMF was removed under reduced pressure and the residue was washed with water to obtain, after filtration, 73 mg of a crude product. Purification by flash chromatography on KH2PO4 buffered silicagel using as eluent CH2Cl2/MeOH 95:5 afforded 24 mg of the title compound as a white solid. M.p. 127-128° C. Rf=0.26 (Merck silica gel 60F254, CH2Cl2:/MeOH 90:10)

Provenance & Evidence