Ammonium Hydroxide → HCID 21075716, compound

Participants

Reaction Steps

tert-Butyl N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)carbamate (14.3 g, 41.8 mmol) was dissolved in 150 mL of 2 M HCl in EtOH, and the reaction mixture was heated to reflux for 3 h. The reaction mixture was cooled and concentrated under reduced pressure to give a brown solid. The brown solid was dissolved in 100 mL of H2O and treated with 100 mL of concentrated NH4OH solution. The basic, aqueous solution was then extracted with CH2Cl2 (4×). The combined organic layers were then washed with brine and dried over Na2SO4. The solution was filtered and concentrated under reduced pressure to give a brown foam. The foam was triturated with Et2O (150 mL) and filtered. The filtrate was concentrated to give 2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-amine (5.77 g) as a tan solid.

Provenance & Evidence