76457-44-8Relevant articles and documents
Reactions of p-Coumaric acid with nitrite: Product isolation and mechanism studies
Torres y Torres, Janelle L.,Rosazza, John P. N.
, p. 1486 - 1492 (2007/10/03)
p-Coumaric acid (1) is an abundant plant phenolic acid, a dietary chemoprotectant, and an antioxidant. The chemoprotective properties of I were demonstrated in vitro by its reaction with NaNO2 in H2O over a range of pH values. The reaction pathway of I with nitrite is dependent on pH. 4-Hydroxybenzaldehyde (3, 16%), 1′,4-dihydroxybenzeneacetaldehyde oxime (5, 59%), and 4-hydroxy-1′-oxo-benzeneacetaldehyde aldoxime (7, 26%) and 7-hydroxy-1,2(4H)-benzoxazin-4-one (11, 6%) were each formed at pH 2, whereas 4-(2-oxido-1,2,5-oxadiazol-3-yl)phenol (13) was formed at pH 3 (6%) and pH 7 and 10 (both 1%). Products were isolated and characterized by NMR and MS spectral analyses. Formation of benzoxazinone (11) requires the 4-phenolic functional group and the conjugated propenoic acid side chain of p-coumaric acid. The mechanism for nitrosation at pH 2 was examined by reacting I in H218O/NaNO2.
Process for the preparation of arylalkylamines and substituted arylalkylamines
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, (2008/06/13)
Arylalkylamines (as the hydrochloride salt), e.g. tyramine hydrochloride, are prepared by hydrogenating substituted or unsubstituted aryl-α-oximinoalkyl ketones, e.g. p-hydroxyisonitroacetophenone, in either in an aqueous reaction medium comprising hydrochloric acid, essentially without the presence of a lower alkyl alcohol in said reaction medium, or in an aqueous reaction medium comprising water, hydrochloric acid, and a lower alkyl alcohol, wherein the alcohol comprises less than about 90% by volume of the reaction medium. A substituent on the aryl portion of the aryl-α-oximinoalkyl ketone must be on a position which activates the aromatic ring.
Process for the preparation of 1-(m- and p-hydroxyphenyl)-2-aminoethanol
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, (2008/06/13)
The present invention relates to a process for the preparation of 1-(m- and p- hydroxyphenyl)-2-aminoethanol which consists of converting an m- or p- hydroxyacetophenone to an isonitrosoketone followed by hydrogenation of the isonitrosoketone. These compounds are sympathomimetics which produce vasoconstricting and cardiotonic effects.
