Chemical Properties
N-Hydroxyphthalimide is yellow moist powder
Uses
Catalyst for oxidation reactions.
Uses
N-Hydroxyphthalimide，additives in to DCC method of peptide synthesis used to improve yield of optically pure product.
Application
N-Hydroxyphthalimide is used in the synthesis of a new class of antibacterials potent against macrolide resistant bacteria. Also used in the synthesis of pyrazolidines, isoxazolidines and tetrahydrooxazines.
reaction suitability
reaction type: Addition Reactions
Synthesis
One method of synthesizing N-Hydroxyphthalimide from phthalic anhydride and hydroxylamine hydrochloride. Using hydrated organic solvent containing organic solvent C4H8O2 in 40-100 vol% as reaction medium system, and through reaction at 60-120 deg.c for 0.5-4 hr, reduced pressure distillation to recover solvent, and drying, the desired product is obtained with the yield of 90-95% and the purity of 97%.
Purification Methods
N -Hydroxyphthalimide [524-38-9] M 163.1, m 230o, ~235o(dec), 237-240o, 7.0. Dissolve the imide in H2O by adding Et3N to form the salt and while hot, acidify, cool and pour into a large volume of H2O. Filter off the solid, wash it with H2O and dry it over P2O5 in a vacuum. [Nefken & Teser J Am Chem Soc 83 1263 1961, Fieser 1 485 1976, Nefkens et al. Recl Trav Chim, Pays-Bas 81 683 1962] The O-acetyl derivative has m 178-180o (from EtOH). [Beilstein 21/11 V 100.]
