Sodium borohydride → HCID 21075809, compound

Participants

Reaction Steps

A solution of N-isopropylidene-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (4.30 g, 16.1 mmol) in 100 mL of methanol was cooled in an ice water bath. The solution was treated with sodium borohydride (3.05 g, 80.7 mmol) over 5 min. The reaction mixture was allowed to warm to ambient temperature. After 2.5, the reaction was quenched by addition of 15 mL of saturated NH4Cl solution. The mixture was concentrated under reduced pressure to yield a light brown solid. The solid was partitioned between 100 mL CHCl3 and 25 mL of saturated NaHCO3 solution and then separated. The organic portion was washed with water (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown solid. The solid was purified by chromatography (SiO2, 97:2.5:0.5 CHCl3:MeOH:NH4OH) to give 2.48 g of N-isopropyl-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine as a tan solid.

Provenance & Evidence