Sodium Hydroxide → HCID 58307299, compound

Participants

Reaction Steps

A mixture of 3-(3,4-methylenedioxyphenylamino)phthalic acid dimethyl ester (0.63 g, 1.9 mmol) and 3N NaOH (50 mL) in ethanol (100 mL) was heated to reflux for 2 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 0.50 g of the product in 88% yield: 1H NMR (DMSO-d6) δ 5.99 (s, 2H), 6.59 (dd, J=8.7 Hz, J=2.1 Hz, 1H), 6.77 (d, J=2.1 Hz, 1H), 6.85 (d, J=8.7 Hz, 1H), 7.04 (dd, J=7.3 Hz, J=0.9 Hz, 1H), 7.13 (dd, J=8.5 Hz, J=0.9 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H), 7.95 (s, 1H).

Provenance & Evidence