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Synthesis of N-Naphthyl-4-Hydroxybenzamides and Their O-Acetylation Derivatives

Liao Qing; Xiao Sen; Zhang Zhilin (Department of Fine Chemicals, Beijing institute of Clothing Technology,Beijing 100029)  
his paper introduces an improved single step direct condensation method of 4hydroxybenzoic acid with arylamine.Ten new N-arylhydroxy benzamides were first synthesized,and may be expressed with the general formula below:1,4-RO-C6H4-CO-NH-C10H6R'(in which RO may be HO-,or CH3COO-;C10H6R'-may be 1-C10H7-,2-C10H7-,1,4-CH3C10H6-,1,4-CIC10H6-,1,4-CH3OC10H6-,1,4-O2NC10H6-).In order to select optimum conditions for the preparation of these benzamides,the systematic orthogonal tests were adopted.The influence of basicity of naphthylamine,the kind of inorganic acyl chloride,the property of the solvents,the reaction temperature and reaction time were systematically studied.Some experiential rules for this reaction was generalized and good synthetic method was proposed.
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