Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Benzodiazepines. XI. Further Examination of the Chromic Acid Oxidation of 2-Aminomethylindoles to 2, 3-Dihydro-2H-1, 4-benzodiazepin-2-ones
SHIGEHO INABAKIKUO ISHIZUMIKAZUO MORIHISAO YAMAMOTO
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1975 Volume 23 Issue 10 Pages 2421-2424

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Abstract
In the chromic acid oxidation of 2-aminomethyl-5-chloro-1-methyl-3-phenylindole (1) to 7-chloro-1, 3-dihydro-1-methyl-5-phenyl-2H-1, 4-benzodiazepin-2-one (2), 1 reacts rapidly with chromic acid to form an oxidation intermediate A, which on acetylation with acetic anhydride gives 2-acetamido-2'-benzoyl-4'-chloro-N-methylacetanilide (3). The rate for formation of 2 from A has been determined by following the change of the quantities of 2 and 3 obtained by periodical sampling followed by quenching with acetic anhydride. The rate is first order with respect to the concentration of A.
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© The Pharmaceutical Society of Japan
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