methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate → methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate

Participants

Reaction Steps

A suspension of 34.2 g (0.069 mol) of methyl 4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]-2,3-dichlorobenzoate and 6.84 g of 10% palladium on carbon in 850 mL of ethyl acetate was shaken under hydrogen at 3 Torr for 1 hour. The mixture was filtered through Celite® and concentrated under vacuum to 300 mL. This solution was washed in turn with 5% sodium carbonate solution, water, and brine and then concentrated to an oil which crystallized on standing. This was dissolved in 25 mL of hot methanol which when cooled gave crystals. The suspension was slowly diluted with water and then filtered to give 24.39 g (96%) of crystals; mp 94°-96° C.

Provenance & Evidence