Traditional Gabriel Synthesis
In this method, the sodium or potassium salt of phthalimide is N-alkylated with a primary alkyl halide to give the corresponding N-alkylphthalimide. The reaction fails with most secondary alkyl halides:
Upon workup by acidic hydrolysis the primary amine is liberated as the amine salt. Alternatively the workup may be via the Ing-Manske procedure, involving reaction with aqueous or ethanolic hydrazine at reflux. This produces a precipitate of phthalhydrazide along with the primary amine. The first technique often produces bad yields or side products; separation of phthalhydrazide can be unpleasant. For these reasons, other methods for liberating the amine from the phthalimide exist. Even with the use of the hydrazinolysis method, the Gabriel method suffers from relatively harsh conditions.
Read more about this topic: Gabriel Synthesis
Famous quotes containing the words traditional and/or synthesis:
“We should have an army so organized and so officered as to be capable in time of emergency, in cooperation with the National Militia, and under the provision of a proper national volunteer law, rapidly to expand into a force sufficient to resist all probable invasion from abroad and to furnish a respectable expeditionary force if necessary in the maintenance of our traditional American policy which bears the name of President Monroe.”
—William Howard Taft (1857–1930)
“If in the opinion of the Tsars authors were to be the servants of the state, in the opinion of the radical critics writers were to be the servants of the masses. The two lines of thought were bound to meet and join forces when at last, in our times, a new kind of regime the synthesis of a Hegelian triad, combined the idea of the masses with the idea of the state.”
—Vladimir Nabokov (1899–1977)