Chloroform → HCID 86594226, compound

Participants

Reaction Steps

A solution of tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)imino]propyl}carbamate (1.64 g, 4.13 mmol) in 20 mL of methanol was treated with NaBH4 (0.78 g, 20.6 mmol) under an atmosphere of nitrogen. After 1.5 h, the reaction mixture was quenched with saturated NH4Cl solution and concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 solution and CHCl3 and the phases were separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light brown solid. Chromatography [SiO2, 95:5 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH)] yielded tert-butyl {3-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.34 g) as a tan foam.

Provenance & Evidence