Sodium Hydroxide → 3-(3-Ethoxy-4-methoxyphenylamino)phthalic acid

Participants

Reaction Steps

A mixture of 3-(3-ethoxy-4-methoxyphenylamino)phthalic acid dimethyl ester (0.85 g, 2.4 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 3 hours. The mixture was cooled, and the solvent was removed under vacuum. The residue was dissolved in water (100 mL), washed with ethyl acetate (3×75 mL), acidified (HCl) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 0.68 g of the product, in 87% yield: 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H), 3.73 (s, 3H), 3.96 (q, J=6.9, 2H), 6.69 (dd, J=8.6 Hz, J=2.4 Hz, 1H), 6.78 (d, J=2.4 Hz, 1H), 6.90 (d, J=8.6 Hz, 1H), 7.00 (d, J=7.2 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.30 (t, J=7.9 Hz, 1H), 7.97 (s, 1H).

Provenance & Evidence