Sodium Hydroxide → Methyl 8-amino-2-naphthoate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 8.0 g (33 mmoles) of 8-acetylamino-2-naphthoic acid, methyl ester (VI) in 50 mL of methanol and 35 mL of 12N HCl was allowed to reflux for 1.5 hours. The reaction mixture was then cooled to 0° C., and pH adjusted to 6.5 with 10N NaOH. Removal of methanol in vacuo followed by collection of precipitate by vacuum filtration followed by washing with H2O and air drying afforded 5.72 g (yield: 80%) of 8-amino-2-naphthoic acid, methyl ester; 1H-NMR: δ8.62 (s, 1H), 7.99 (dd, J=8.5 Hz, 1.4 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.36 (m, 1H), 7.25 (d, J=8.4 Hz, 1H), 6.79 (d, J=7.1 Hz, 1H), 4.35 (bs, 2H), 3.95 (s, 3H); MS (DCI) m/e: 218 (MH+).

Provenance & Evidence