The values of pseudo first-order rate constants (k obs ) for the cleavage of N-(2-hydroxyphenyl)phthalamic acid (7), obtained at 4.9 × 10 −2 M HCl, 35 • C, and within CH 3 CN content range 2-80% (v/v) in mixed aqueous solvent are smaller than k obs for the cleavage of N-(2-methoxyphenyl)phthalamic acid (8) INTRAMOLECULAR CARBOXYLIC GROUP-ASSISTED CLEAVAGE 747 by nearly 1.5-to 2-fold. These observations show the absence of expected intramolecular general acid catalysis due to 2-OH group in 7. The values of k obs for the cleavage of 7 and 8 decrease by more than 20-fold with the increase in the content of CH 3 CN from 2 to 80-82% (v/v) in mixed aqueous solvent. The kinetic data reveal that in acidic aqueous cleavage of 7, N-cyclization (leading to the formation of imide) and O-cyclization (leading to the formation of phthalic anhydride) vary from ∼10 to 15% and ∼90 to 85%, respectively, with the increase in CH 3 CN content from 2 to 80% (v/v). Similar increase in CH 3 CN content causes increase in N-cyclization from ∼0 to 5% and decrease in O-cyclization from ∼100 to 95% in the acidic aqueous cleavage of 8. Some speculative, yet conceivable, reasons for nearly 10 and 0% N-cyclization in the cleavage of respective 7 and 8 at low content of CH 3 CN have been described.