Tetrahydrofuran → HCID 22386478, compound

Participants

Reaction Steps

An emulsion of 1.2 g (4.8 mmol) E/Z-3-[3-(pyridin-3-yl)propylidene]isobenzofuran-1(3H)-one and 15 ml hydrazine hydrate in 15 ml THF is stirred for 2 h at 80° C. (oil dissolves). The cooled reaction mixture is diluted with 50 ml EtOAc, the aqueous phase separated off, extracted twice with 50 ml EtOAc and discarded. The organic phases are extracted 3 times with 20 ml 1 N HCl and likewise discarded. The combined HCl extracts are adjusted to alkaline pH with 1 N NaOH and extracted 3 times with 50 ml EtOAc each time. Drying (Na2SO4) and evaporation of the organic phases yield, after crystallization from EtOAc/DIPE, the title compound; m.p. 142° C.; 1H-NMR (CDCl3) 10.45 (s, HN), 8.47 (m, 3H), 7.8 (m, 3H), 7.53 (dt, 1H), 7.22 (dd, 1H), 2.98 (t, 2H), 2.77 (t, 2H), 2.15 (quin., 2H); FAB-MS (M+H)+=266; anal. calc. (C16H15N3O) C, 72.43%; H, 5.70%; N, 15.84%; meas. C, 72.04%; H, 5.68%; N, 15.47%.

Provenance & Evidence