2-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline → HCID 19419852, compound

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Reaction Steps

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.5 g) in piperidine (20 ml) was stirred under reflux, under nitrogen, for four hrs. The reaction mixture was quenched with dilute sodium bicarbonate solution (200 ml) and the aqueous suspension was extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by high performance liquid chromatography (silica gel; 3:1 dichloromethane-ethyl acetate). The appropriate fractions were collected and concentrated. This residue was dissolved in ether and treated dropwise with a solution of hydrogen chloride/ether. The precipitate was collected and washed with ether to give 4.3 g (85%) of product, mp 260° C.

Provenance & Evidence