Sodium Hydroxide → HCID 19363338, compound

Participants

Reaction Steps

Ethyl 4-chloro-7-methoxy-8-pentyloxyquinoline-3-carbamate (311 mg, 0.84 mmol), ethanol (3 ml) and a 1N aqueous sodium hydroxide solution (3 ml) were mixed, and this solution was refluxed under heating for 0.5 hour. Ethanol was evaporated under reduced pressure, and conc. hydrochloric acid was added to make the reaction mixture acidic. THF (10 ml) and ethyl acetate (10 ml) were added to dissolve the precipitated crystals. The organic layer was separated, washed 3 times with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethanol to give 4-chloro-7-methoxy-8-pentyloxyquinoline-3-carbamic acid (229 mg, 80%) as pale-yellow crystals.

Provenance & Evidence