- Syntheses of 5-benzylamino>-9-N,N-dialkylaminobenzophenoxazonium Chlorides
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Reaction of 4-benzylidene-4'-N,N-dimethylaminoaniline (I) with 4-nitrobenzaldehyde in ethanol induces an aldehyde exchange reaction to provide 4-benzaldehyde (II) in crystalline form. 4-benzylidene-α-naphthylamine (IV) obtained by reaction of II with α-naphthylamine, on reduction with sodium amalgam gives 4-benzyl-α-naphthylamine (V).Condensation of V with 5-dimethylamino-2-nitrosophenol and 5-diethylamino-2-nitrosophenol in HCl affords 5-benzylamino>-9-N,N-dimethylaminobenzo phenoxazonium chloride hydrochloride (VI) and 9-N,N-diethylamino analogue (VII), respectively.Treatment of VI and VII with thionyl chloride furnishes 5-benzylamino>-9-N,N-dimethylaminobenzophenoxazonium chloride hydrochloride (VIII) and 9-diethylamino analogue (IX), respectively.The aldehyde exchange method is found to be a useful variant in the preparation of 4-N,N-dimethylaminobenzaldehyde.
- Sen, A. K.,Mukhopadhyay, Sankardeb
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p. 642 - 645
(2007/10/02)
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