Hydrochloric Acid → 1-(4-Dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To the suspension of 1-(4-dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (31 mg, 0.082 mmol) in methanol (2 mL) was added 25% of aqueous sodium hydroxide solution (0.27 mL, 1.68 mmol). The mixture was stirred at 90° C. for 12 h. After cooling to room temperature, the reaction was adjusted to pH=2 with 2 N HCl solution. The product was extracted with chloroform (2×200 mL). The combined organic layers were washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified directly by HPLC (Reverse C18, 10%–90% acetonitrile in water in 10 min) afforded our desired product 1-(4-dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid (9 mg) as a solid. LC/MS m/e calcd for C25H22N2O5 (MH+) 431. found 431.

Provenance & Evidence