Ethyl orthoformate → HCID 68970165, compound

Participants

Reaction Steps

7-Benzyloxy-1,2-dimethyl-1H-imidazo[4,5-c]quinoline was prepared according to the methods described in Parts A-C of Example 31. In Part C, triethyl orthoformate was used in lieu of trimethyl orthovalerate. A solution of 7-benzyloxy-1,2-dimethyl-1H-imidazo[4,5-c]quinoline in ethanol was added to a Parr vessel with 10% palladium on carbon. The reaction was placed under hydrogen pressure (35 psi, 2.4×105 Pa) for 20 hours. The reaction mixture was then filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure. The residue was dissolved in acetic acid with heating, and the hot solution was filtered and concentrated under reduced pressure. The resulting beige solid was dissolved in 1 N aqueous hydrochloric acid, and deactivated carbon was added. The solution was heated, filtered, and treated with 50% aqueous sodium hydroxide. A precipitate formed and was isolated by filtration to provide 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-ol as a solid, mp >300° C.

Provenance & Evidence