Application of Pschorr reaction to N-(o-aminobenzoyl)-benzyl and phenethyl amines and to N-(o-aminophenylacetyl) anilines

Abstract

Decomposition of the diazonium chloride from N-(o-aminobenzoyl)-N-methylbenzylamine led to the formation of 3-benzyl-3, 4-dihydrobenzo-triazin-4-one (8), N-benzoylbenzylamine (11), N-benzylphthalimidine (13) ando-diphenic acid N-methyl amide (14), the last one presumably through the intermediary, the expected dibenzazepinone 16. From the analogue, N-(o-aminobenzoyl)-4-methoxybenzyl amine (4), triazinone 10 and N-benzoyl-4-methoxybenzyl amine (12) were obtained. Application of Pschorr reaction to N-(o-aminobenzoyl)-N-methyl-β-(4-methoxyphenyl) ethyl amine (23) afforded 2-methoxy-7-methyl-5, 6, 7, 8- tetrahydrodibenzo (c, e) azocin-8-one (26), with an interesting conformation. From N-(o-aminophenylacetyl)-p-methoxyaniline were obtained under these conditions, indazole-3-carboxylic acidp-anisidide (35) and N-[2-(4-methoxyphenyl carbamoylmethyl) phenyl]-1-(p-methoxyphenyl) isatin-β-hydrazone (37). The structure of 37 was deduced from spectral data and hydrolysis to the acid 42. Diazotisation of N-(o-aminophenylacetyl)-1, 2, 3, 4-tetrahydroquinoline (47) led to the formation of tetrahydroquinoline (49) ando-hydroxyphenyl acetic acid (50) presumably through the salicylamide 48. A similar reaction on N-(o-aminophenylacetyl) tetrahydroisoquinoline (52) gave the benzofurandione hydrazone 55, besides tetrahydroisoquinoline. Oxindole 45 and benzofuranone 56 were likely precursors for 37 and 55 respectively. Salicylamides 5, 7, 24 and 34 were byproducts in the Pschorr reaction.