Acetone → HCID 14708756, compound

Participants

Reaction Steps

A mixture of 3.7 g. sodium 6-nitroindazolide, 4.58 g. of methyl 4-bromomethylbenzoate (F) and 120 ml. acetone was heated under reflux in a nitrogen atmosphere for 54 hours and then diluted with 250 ml. ethyl acetate and 40 ml. of 50% w/v brine. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated to give a brown solid. Early fractions from chromatography of the solid on a Waters 500 HPLC (SiO2, 25% v/v ethyl acetate in hexane) yielded a solid which was crystallized from ethyl acetate to give methyl 4-(6-nitroindazol-1-yl)methylbenzoate (J) as light yellow needles, 1.71 g. (28%); m.p. 171°-172.5° C.; partial 13C-NMR: 134.10 (C-3).

Provenance & Evidence