A kinetic study on hydrolysis of N-(2 -hydroxyphenyl)phthalamic acid (1), N-(2 -methoxyphenyl)phthalamic acid (2), and N-(2 -methoxyphenyl)benzamide (3) under a highly alkaline medium gives second-order rate constants, k OH , for the reactions of HO − with 1, 2, and 3 as (4.73 ± 0.36) × 10 −8 at 35 • C, (2.42 ± 0.28) × 10 −6 and (5.94 ± 0.23) × 10 −5 M −1 s −1 at 65 • C, respectively. Similar values of k OH for 3, N-methylbenzanilide, N-methylbenzamide, and N,N-dimethylbenzamide despite the difference between pK a values of aniline and ammonia of ∼10 pK units are qualitatively explained.