Iodine → HCID 14281027, compound

Participants

Reaction Steps

A solution of 5-[[5-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-2-nitrophenyl]methylene-2,4-imidazolidinedione (12 g, 26 mmol) in dimethylformamide (200 mL) was hydrogenated at 55 p.s.i. over 10% palladium on charcoal (1.2 g) in a low pressure hydrogenation apparatus. After 40 hours, the mixture was filtered through kieselguhr, the solvent evaporated and the residue suspended in refluxing methanol. Iodine (6.69 g, 26 mmol) was added portionwise over 4 minutes, reflux continued for 10 minutes, and the mixture then concentrated in vacuo to approximately 70 mL. 10% Sodium thiosulate solution and 10% sodium carbonate solution was added, the mixture stirred for 5 minutes and a solid filtered off, washed with water and dried in air. This was dissolved in hot dimethylformamide and water added to precipitate a solid (4.80 g) which was dissolved in 10% hydrogen chloride in methanol. The methanol was removed and the residue crystallized from ethanol to give the hydrochloride salt of 7-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one (2.16 g, 18% overall), m.p. 288°-291° C.

Provenance & Evidence