SYNTHESIS OF 4-(4-DI SUBSTITUTED AMINO(PHENYL) METHYL)1-3-HYDROXY NAPHTHALEN -2-OL)DIZENYL

The reaction between 2-naphthol, aryl aldehydes and ammonia or amines yields aminobenzyl naphthols in process known as Betti reaction; this procedure can be interpreted as extension of the Mannich condensation, with formaldehyde replaced by aromatic aldehydes, secondary amine by ammonia and the C – H acid by an electron-rich aromatic compound such as 2-naphthol. 1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines were prepared through reactions of 2-naphthol, aromatic aldehydes and amines in ratio 1:2:1 in presence of methanol. Acid hydrolysis of 1,3-naphthoxazines using 20% HCl produce derivatives of Betti bases, Betti bases were prepared directly via the reaction between 2–naphthol, benzaldehyde and ammonia solution or aliphatic amines (primary and secondary) in ratio 1:1:1 in presence of water. Some of the Betti base derivatives which were synthesized by the two methods reacted with diazonium salts and produce colour compounds in moderate to high yield known as azo dyes. The structures of the all synthesized compounds were confirmed by IR, H1-NMR, and MS spectral studies. Results of this study revealed that, the Betti base derivatives which were synthesized directly or via 1,3-naphthoxazines showed the same physical properties and spectral behaviour