Process for producing aromatic amide compounds useful as cyan coupler for color photographes
申请人:SUMITOMO CHEMICAL COMPANY, LIMITED
公开号:EP0608896A1
公开(公告)日:1994-08-03
There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture. Also disclosed is another process for producing an aromatic amide compound of the general formula (4), including the step of subjecting an o-aminophenol hydrochloride salt of the general formula (6) to condensation with an acid chloride compound having a sulfur content of 0.8% or less, based on the weight of the acid chloride compound, of the general formula (3) in an inert solvent.
本发明公开了一种生产通式(4)的芳香族酰胺化合物的工艺,包括以下步骤:(a) 在镍催化剂存在下,将通式(1)的邻硝基苯酚化合物在丙酮或芳香烃溶剂中进行催化还原,得到通式(2)的邻氨基苯酚化合物;(b) 将通式(2)的邻氨基苯酚化合物与硫含量为 0.5%或更低的通式(3)的酸性氯化物在丙酮或芳香烃溶剂中,在氧浓度为 1%或更低的惰性气体气氛下进行缩合。硫含量为 0.5%或更低的通式(3)的酸性氯化物可以通过让通式(5)的羧酸化合物与亚硫酰氯反应并浓缩反应混合物来获得。还公开了另一种生产通式(4)芳香族酰胺化合物的工艺,包括在惰性溶剂中使通式(6)的邻氨基苯酚盐酸盐与硫含量为 0.8%或以下(以氯化酸化合物重量为基准)的通式(3)氯化酸化合物缩合的步骤。