Acetic Acid → N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (6.91 g, 19.8 mmol) in 55 mL of acetonitrile was treated with 2,2-dimethoxypropane (12.2 mL, 99.2 mmol) and 14 mL of glacial acetic acid. The reaction mixture was heated to 100° C. under an atmosphere of nitrogen. After 22 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a brown oil. The oil was dissolved in 125 mL of CHCl3 and washed with saturated NaHCO3 solution (2×30 mL) and water (30 mL). The combined aqueous washes were back-extracted with CHCl3 (25 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 7.69 g of N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine as a brown solid.

Provenance & Evidence