Inventors:
Neil J. O'Reilly - Grand Island NY
Stanley A. Sojka - Buffalo NY
Henry C. Lin - Grand Island NY
Assignee:
Occidental Chemical Corporation - Niagara Falls NY
International Classification:
C07C21127
Abstract:
2-Chlorobenzylamine is prepared from 2-chlorobenzylchloride in a two-step process. In the first step, 2-chlorobenzylchloride is reacted with alkali metal phthalimide, preferably formed in situ from potassium carbonate and phthalimide, to form the novel intermediate 2-chlorobenzylphthalimide. In the second step, the phthalimide ring of the 2-chlorobenzylphthalimide is cleaved to form 2-chlorobenzylamine. The first step is preferably carried out in an unreactive solvent at 60. degree. C. to reflux temperature, for example, for 1 to 10 hours. The solvent is very preferably dimethylformamide which is advantageously recovered and used again as solvent in the conversion of 2-chlorobenzylchloride to 2-chlorobenzylphthalimide. The second step consists essentially, for example, of hydrazinolysis or hydrolysis. When the second step consists essentially of hydrazinolysis, the 2-chlorobenzylphthalimide is reacted with hydrazine to form 2-chlorobenzylamine and phthalylhydrazide, and the 2-chlorobenzylamine is separated by reacting with acid to form soluble amine salt, filtering out the phthalylhydrazide and then reacting the amine salt with base to convert it to the free amine.