Water → 4-(4-Nitrophenoxy)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,4-dihydroxy-pyridine (2.33 g, 21 mmol), 4-fluoro-nitrobenzene (2.22 ml, 21 mmol) and Cs2CO3 (10.2 g, 31.3 mmol) in N-methyl-pyrrolidine (30 ml) is stirred for 3 h at 100° C. under N2-atmosphere. The reaction mixture is poured into water and the precipitate filtered off and washed with water. The solid is dissolved in CH2Cl2/MeOH. Then SiO2 (≈20 g) is added and the mixture Is concentrated in vacuo. The resulting powder is put on top of a SiO2-column and eluted with toluene/AcOEt 3:1→AcOEt→AcOEt/EtOH 9:1, yielding the title compound: m.p.: 227-228° C.; 1H-NMR (DMSO-d6): 11.60 (s, HN), 8.31 (d, 2H), 7.47 (d, 1H), 7.39 (d, 2H), 6.07 (dd, 1H), 5.67 (d, 1H).

Provenance & Evidence