Lithium Hydroxide → 1-Amino-4-bromo-2-naphthoic acid

Participants

Reaction Conditions

Reaction Steps

Methyl 1-amino-4-bromo-2-naphthoate hydrobromide was prepared as described in Example 1. To a solution of methyl 1-amino-4-bromo-2-naphthoate hydrobromide (2.00 g, 5.54 mmol) in 20 mL of THF was added sodium hydroxide (11.1 mL, 20% aqueous, 55.4 mmol). Alternatively, lithium hydroxide could be used. The mixture was stirred at 50° C. for 20 h, then heated at 90° C. for 2 h. The solvent was removed in vacuo and hydrochloric acid (1 N aqueous) was added until pH ˜2. The beige solid was collected via filtration, washed twice with water, and dried to provide 1-amino-4-bromo-2-naphthoic acid that gave a mass ion (ES+) of 266.0 (79Br) for [M+H]+.

Provenance & Evidence