Triphenylphosphine → 4-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol

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Reaction Steps

Triphenylphosphine (4.5 g, 17.0 mmole) was added to a mixture of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol (2.4 g, 8.5 mmole, Example 9) and 1,2-dichlorobenzene. The reaction mixture was heated at reflux for 3 hrs then concentrated under vacuum. The residue was combined with methanol (400 mL) and hydrochloric acid (50 mL of 0.5N) then heated on a steam bath for 2 hours. The resulting precipitate was isolated by filtration then washed with ether. The solid was dissolved in water and the solution was made basic with 10% sodium hydroxide. After stirring for 30 minutes, the reaction mixture was filtered. The collected solid was rinsed with water and ether then recrystallized from N,N-dimethylformamide/ethanol to provide about 1 g of 4-amino-α,αdimethyl-1H-imidazo [4,5-c]quinoline-1-ethanol as a solid, m.p. 271-273° C. Analysis: Calculated for C14H16N4O: % C, 65.6; % H, 6.29; % N, 21.86; Found: % C, 65.37; % H, 6.26; % N, 21.61.

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