Sodium Hydroxide → 3-(2,4-Dimethoxyphenylamino)phthalic acid

Participants

Reaction Steps

A mixture of 3-(2,4-dimethoxyphenylamino)phthalic acid dimethyl ester (0.85 g, 2.5 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 90 minutes. 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 0.76 g in 97% yield: 1H NMR (CDCl3) δ 3.82 (s, 3H), 3.84 (s, 3H), 6.52 (dd, J=8.6 Hz, J=2.5 Hz, 1H), 6.57 (d, J=2.5 Hz, 1H), 7.11 (d, J=8.6 Hz, 1H), 7.22-7.26 (m, 2H), 7.52 (t, J=7.8 Hz, 1H), 7.61 (br, 1H).

Provenance & Evidence