alpha,alpha-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol → HCID 9903314, compound

Participants

Reaction Steps

A catalytic amount of platinum (IV) oxide was added to a solution of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol (0.40 g, 1.4 mmole, Example 1) in trifluoroacetic acid (10 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) for 48 hours. The catalyst was removed by filtration and washed with ethanol. The filtrate was concentrated under vacuum using heptane to azeotrope the trifluoroacetic acid. The resulting oil solidified on standing. The solid was dissolved in water containing enough hydrochloric acid to form a salt of the product. The aqueous solution was filtered through charcoal. The filtrate was made basic with ammonium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 0.3 g of 4-amino-α,α-dimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as a white solid, m.p. 259.8°-261.3° C. Analysis: Calculated for C14H20N4O: % C, 64.59; % H,7.74; % N, 21.52; Found % C, 64.49; % H, 7.63; % N, 21.41.

Provenance & Evidence