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The synthesis of 2,6‐dichlorobenzylidene aminoguanidine acetate [α‐ 14 C]
Author(s) -
Sisenwine Samuel F.,
Tio Cesario O.,
Ahern Jenny
Publication year - 1976
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580120404
Subject(s) - chemistry , nitrile , aldehyde , steric effects , lithium (medication) , medicinal chemistry , bicarbonate , chemical synthesis , organic chemistry , catalysis , medicine , biochemistry , in vitro , endocrinology
2,6‐Dichlorobenzylidene aminoguanidine acetate, a new antihypertensive agent, was labelled with 14 C at the benzal position for metabolic studies. The key reaction involved the reduction of the sterically hindered 2,6‐dichlorobenzonitrile [cyano‐ 14 C] with lithium aluminum hydride to 2,6‐dichlorobenzaldehyde [carbonyl‐ 14 C]. The labelled nitrile was prepared by a Sandmeyer reaction employing 2,6‐dichloroaniline and K 14 CN. Further reaction of the labelled aldehyde with aminoguanidine bicarbonate produced the desired radioactive drug.