N-bromobutanimide → HCID 9977862, compound

Participants

Reaction Steps

2 g (6.36 mmol) of 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline (Example 25), 6.6 g (37 mmol) N-bromosuccinimide, and 1.32 g (4.45 mmol) FeBr3 (98%; Aldrich) are heated and kept under reflux during 2½ h in 50 ml CHCl3. The cold solution is poured on ca. 300 ml ice-water, where a precipitate is formed. Extraction of the water phase with CH2Cl2 and chromatography of the raw material on silicagel (hexane-ethyl acetate 1:1) gives the desired title compound. mp: 183-192° C.; MS: 392 (M++1); HPLC: tret=12.44 min (Grad 1).

Provenance & Evidence