Sodium Hydroxide → 4-[[(1,1-Dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoic acid

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Reaction Steps

Methyl 4-[[(1,1-dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoate (325 mg, 0.82 mmol), 4.1 mL of 2N NaOH in 10 mL of tetrahydrofuran and 10 mL of methanol were stirred for 2 hours. The mixture was concentrated and acidified with 1N HCl (20 mL), extracted with ethyl acetate (35 mL×2). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was triturated in ether-hexane to give 246 mg (78% yield) of the title compound as white solids; NMR (DMSO-d6) δ1.35 (s, 6H), 6.58 (s, 1H), 7.38-7.70 (m, 7H), 7.73 (d, J=7.9 Hz, 1H), 7.90 (s, 1H), 8.04 (s, 4H), 10.38 (bs, 1H), 13.25 (bs, 1H); MS m/e 384 (MH+).

Provenance & Evidence