Aromatic Amino Carboxylic Acid의 Diazo化에 관한 연구

Abstract

It has been reported that diazotized amines decompose in the presence of certain reducing agents to form the common replacement derivatives with other products, including biaryls. o-, m- and p- Chlorobenzoic acids were synthesized starting from o-, m- and p- aminobenzoic acids through the extended Sandmeyer reaction, respectively. The experiment was intended to know the optimum concentration of cuprous chloride solution in hydrochloric acid according to various normalities ( 12N, 10N, 8N, 6N, 4N and 2N ) when the diazotized. amine was replaced with chloride radical. The yIeld of chlorobenzoic acid considerably varied with the normality and volume of cuprous chloride solution. In the case of o- and p- chlorobenzoic acid, their maximum yields were 71.9% and 90.6% at 6N HCl, respectively. Whils the maximum yield of m-chlorobenzoic acid was 77.2% at 4N HCl. When the diazotized amine was also replaced with cyanide radical, p-cyanobenzoic acid synthesized with Sandmeyer reaction was yielded 44.3% and with tetracyanonickelate(ll)ion was yielded 41.3%.