Hydrochloric Acid → HCID 22048438, compound

Participants

Reaction Steps

To a solution of 1-(3-isopropoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid (198 mg) in 8 ml of tert-butanol was added diphenylphosphoryl azide (DPPA, 0.119 ml, 1.10 eq) and triethylamine (0.084 ml, 1.20 eq). The mixture was refluxed for 3 hrs and then solvents were evaporated. The residue was extracted with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried and then evaporated. The residue was dissolved in a mixture of 4 ml of methylene chloride and 4 ml of trifluoroacetic acid. The mixture was kept at room temperature for 1 hr and then solvents were evaporated. The residue was extracted with ethyl acetate and saturated sodium bicarbonate solution. After the evaporation of solvents, the residue was purified through a flash column chromatography using ethyl acetate and hexane (2/1 ratio) to give an oil. This oil was dissolved in methylene chloride and hydrogen chloride (gas) in ether was added. After the evaporation of solvents, a yellow solid was obtained as 1-(3-isopropoxybenzoyl)-4-amino-6,7-dimethoxyisoquinoline hydrochloride (106 mg, 48% in two steps).

Provenance & Evidence