Methanol → HCID 21075787, compound

Participants

Reaction Steps

A solution of 2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (1.50 g, 6.19 mmol) in 20 mL of toluene and 5 mL of isopropanol was treated with 3-pentanone (5.00 mL, 47.2 mmol) and pyridinium p-toluenesulfonate (0.015 g, 0.062 mmol) and the reaction mixture was heated to reflux under an atmosphere of nitrogen. After 7 d, the reaction mixture was concentrated under reduced pressure, dissolved in CHCl3, washed with water (2×) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown oil. Chromatography (SiO2, 95:5 CHCl3:MeOH) gave N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(1-ethylpropylidene)amine (1.78 g) as a yellow/green syrup.

Provenance & Evidence