Hydrochloric Acid → HCID 67520377, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-amino-6-hydroxy-1-naphthoate (0.500 g, 2.30 mmol) in THF (2.5 mL) was cooled to 0° C. and 3 N HCl (5.0 mL) was added. A solution of sodium nitrite (0.175 g, 2.53 mmol) in water (1.2 mL) was added and the mixture stirred at 0° C. for 15 min. A solution of potassium iodide (0.764 g, 4.60 mmol) in water (1.2 ml) was added and the mixture was stirred at 0° C. for 1 h. EtOAc was added and the solution was poured into water. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford a red-brown oil. This material was purified via column chromatography on silica gel (eluting with 0-50% EtOAc-hexane) to afford methyl 6-hydroxy-4-iodo-1-naphthoate as a tan solid. MS (ESI, pos. ion) m/z: 328.8 (M+H). Mass Calc'd for C12H9IO3: 328.

Provenance & Evidence