Hydrochloric Acid → (3-((Methylsulfonyl)amino)phenyl)acetic acid

Participants

Reaction Steps

Methyl 3-(methanesulfonylamino)phenylacetate (3.36 g, 13.8 mmol) was dissolved in ethanol (16 mL) and 1N NaOH (30 mL) added. The reaction was stirred for 1 hour, then 1N HCl (50 mL) and water (50 mL) were added. The product was extracted into ethyl acetate (3×50 mL) and the combined extracts were washed with water and brine and dried (MgSO4). Removal of solvent afforded 3-(methanesulfonylamino)phenylacetic acid (2.90 g, 92%). 1H NMR (DMSO-6) δ 12.32 (1H, br), 9.69 (1H, br), 7.26 (1H, dd), 7.10 (2H, m), 7.00 (1H, d), 6.57 (1H, s), 3.54 (2H, s), 2.97 (3H, s).

Provenance & Evidence