Lithium Hydroxide → 8-(Aminomethyl)naphthalene-2-carboxylic acid

Participants

Reaction Steps

To a solution of methyl 8-aminomethyl-2-naphthoate (0.75 g, 0.0035 mol) in dry tetrahydrofuran (50 mL), cooled to 0° C., was added a solution of lithium hydroxide (0.5M, 5.83 mL). All was stirred at ambient temperature over 20 hours. Another aliquot of lithium hydroxide was added and all was stirred for an additional 20 hours. The solid was collected and the filtrate was evaporated to dryness under reduced pressure. The solids were triturated with diethyl ether to give 8-aminomethyl-2-naphthoic acid (0.67 g, 0.0033 mol, 95%) as a white solid. mp=223°-225° C.; 1H NMR (DMSO) d 8.6 (s, 1H), 8.1-7.9 (m, 1H), 7.8-7.7 (m, 4H), 7.55-7.5 (m, 1H), 7,45-7.35 (m, 2H), 4.2 (s, 2H).

Provenance & Evidence