1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-ol

Participants

Reaction Steps

A mixture of 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.2 g, 9.6 mmol) and 10% palladium on carbon (0.15 g) in ethanol (125 mL) was placed under hydrogen pressure (30 psi, 2.1×105 Pa) and shaken on a Parr apparatus for 80 minutes. After 40 minutes the hydrogen pressure had decreased to 20 psi, (14×105 Pa). The reaction mixture was filtered through a layer of CELITE filter agent, and the filtrate was concentrated under reduced pressure. The residue (2.4 g) was recrystallized three times from methanol/water and dried overnight in a vacuum oven at 70° C. to provide 4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-ol as white crystals, mp 232-235° C.

Provenance & Evidence