Potassium phthalimide, 98+%, Thermo Scientific Chemicals

General References:

1. For an example of the classical Gabriel synthesis of primary amines from an alkyl halide by alkylation of potassium phthalimide followed by hydrolysis, see: Org. Synth. Coll., 2, 25 (1943). For use of the Gabriel reaction on Merrifield resin as the first step of a synthesis of a polymer-supported carbodiimide, see: Org. Synth. Coll., 6, 951 (1988). The phthalimide alkylation is often carried out in DMF. A liquid-liquid phase-transfer method using (n-Hexadecyl) tri-n-butyl phosphonium bromide, L01335, as catalyst also gives excellent results: Synthesis, 389 (1976).
2. The standard method for cleavage of the N-substituted phthalimide is with hydrazine hydrate, effective under milder conditions than acid or base hydrolysis. Other hydrazines and primary amines have also been successful, e.g. methylhydrazine or N,N-dimethylpropanediamine: Org. Synth. Coll., 9, 13, 16 (1998). Another technique involves borohydride reduction to the hydroxy amide, and liberation of the amine with acetic acid, with cyclization to phthalide: Tetrahedron Lett., 25, 2093 (1984). For suggested improvements to the cleavage conditions in the Gabriel synthesis, see: J. Org. Chem., 61, 8063 (1996). Review of the Gabriel reaction: Angew. Chem. Int. Ed., 7, 919 (1968).
3. For an alternative approach to the formation of primary amines, see Dibenzyl amine, A11554.
4. Kiyokawa, K.; Kosaka, T.; Kojima, T.; Minakata, S. Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions. Angew. Chem. Int. Ed. 2015, 127 (46), 13923-13927.
5. Fesenko, A. A.; Trafimova, L. A.; Albov, D. V.; Shutalev, A. D. Nucleophile-dependent diastereoselectivity in the ring expansion of pyrimidines to give 1,3-diazepines. Tetrahedron Lett. 2015, 56 (11), 1317-1321.