Imidazole → Clioquinol, o-(tert-butyldimethylsilyl)-

Participants

Reaction Steps

A flame-dried, 50-mL, three-necked flask is charged with 5-chloro-8-hydroxy-7-iodoquinoline (2.814 g), which is commercially available, t-butyldimethylchlorosilane (1.76 g), and 10 mL of DMF. Imidazole (1.66 g) is added, and the resulting mixture is stirred at room temperature for 18 h. The reaction mixture is then quenched with 10 mL of saturated aqueous NaHCO3 and extracted with hexane three times. The combined organic layers are dried over MgSO4, filtered and concentrated to give 3.898 g of the title compound as a pale green solid.

Provenance & Evidence