Sodium Hydroxide → HCID 22048284, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [1-(3-sec-butoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid methyl ester (170 mg, 0.39 mmol) in methanol (3.5 mL) was added 1.0 N sodium hydroxide solution (2.0 mL, 1.56 mmol). The reaction mixture was heated at 90° C. for 1 h, concentrated in vacuo and diluted with water (3 mL). The aqueous phase was extracted with diethyl ether (1×10) and then acidified to pH=4 by addition of 1N hydrogen chloride solution. The aqueous phase was then extracted with dichloromethane (3×15 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. HPLC purification afforded [1-(3-sec-butoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid trfluoroacetic acid salt (59 mg, 36% yield) as a light yellow solid. HR-MS m/e calcd for C24H15N1O6 (M−H+) 424.1755, found 424.1758; 1H NMR (300 MHz) compatible.

Provenance & Evidence