Hydrazidic halides, part IV (1). The solvolyses of p-substituted benzhydrazidic bromides
✍ Scribed by F.L. Scott; J.B. Aylward
- Book ID
- 104223187
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 241 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
p-Substituted benzhydrazidic bromides (I) can be made by bromination of the appropriate arylidine p-nitrophenylhydrazones in acetic acid solution. I The reaction conditions used generally involved treating a suspension of the appropriate hydrazone (4 m.moles) in 100 ml. of glacial acetic acid with a solution of 8 m.moles of bromine in 2Oml. of the same solvent (added slowly with vigorous stirring). The benzhydrazidic bromides (I) are formed in ca. 60$ yields. More vigorous reaction conditions, in particular the use of a four-fold excess of bromine and higher reaction temperatures leads to the introduction of an additional bromine atom meta to the nitro group. The only previous report on the bromination of an arylldine p-nitrophenylhydrazone vas that of Gibson (2). He used the benzaldehyde derlvative and reported the formation of a dibromo compound. Compounds of type I are readily hydrolysed to the corresponding aroyl hydrasides (II), after being refluxed in 50$ aqueous dioxan