Hydrochloric Acid → 4-(2-Aminobenzyl)phthalic acid dimethyl ester

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Reaction Steps

2N hydrogen chloride in diethyl ether (1 ml) was added to a solution of 4-(2-(tert-butoxycarbonylamino)benzyl)phthalic acid dimethyl ester (100 mg, 0.25 mmol) in methanol (1 ml). The mixture was stirred for 2 hours at room temperature and evaporated to dryness in vacuo. The crude product was recrystallized from diethyl ether/ethyl acetate to give light, golden crystals of 4-(2-aminobenzyl)phthalic acid dimethyl ester (yield: 69 mg (86%)). 1H—NMR (CDCl3) in ppm: δ 7.74 (1H,d); 7.60 (1H,s); 7.54 (1H,d); 7.27 (2H,d); 7.13 (1H,m); 7.05 (1H,d); 4.12 (2H,s); 3.8 (6H,2xs); 2.5 (3H,s). LC-MS: m/e 322 (M+Na), 300 (MH+).

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