Document Type
Thesis
Date of Award
6-30-1957
Degree Name
Master of Science in Chemical Engineering - (M.S.)
Department
Chemical Engineering
First Advisor
Saul I. Kreps
Second Advisor
C. L. Mantell
Third Advisor
James A. Bradley
Abstract
This study presents an attempt to evaluate the Hofman degradation as a method of synthesizing 3,4-diamino-pyridine from isoquinolinic acid. Since the pyridine ring is known to he stable under the reaction conditions, and analogous aromatic diamides have been prepared by previous investigators, the major problem studied is the effect of hypohalites on ortho-oriented aromatic diamides.
Three methods of approaching the problem were unsuccessful in producing the desired diamine, but the last method, stepwise degradation of each group separately, may be workable with some changes.
The most significant result was the observation of an unexpected side reaction when the diamide was treated with alcoholic hypobromite. In this case deamination of the diamide to an imide took place under mild temperature conditions, apparently as a result of reaction with the hypobromite. This reaction predominated rather than the expected conversion to the corresponding amino acid reported by many investigators under different reaction conditions. No evidence was found of this reaction under other conditions used in this investigation.
Recommended Citation
Zbinden, Harry William, "An investigation of the Hofman reaction as a possible method of synthesizing 3,4-diamino pyridine" (1957). Theses. 2619.
https://digitalcommons.njit.edu/theses/2619
