GB865720A - Improvements in photographic colour couplers - Google Patents

Abstract

1-Methyl-3-[a -(4-a -(2, 4-di-t-amylphenoxy) butyramido phenoxy) acetamido]-5-pyrazolone is prepared by reacting 1-methyl-3-(4-aminophenoxyacetamido)-5-pyrazolone with a -(2, 4-di-t-amylphenoxy) butyryl chloride. The same pyrazolone, the corresponding 1-n-hexyl-pyrazolone, 1-methyl-3-[g -(p-aminophenoxy) butyramido]-5-pyrazolone and 1-n-dodecyl-3-amino-5-pyrazolone are similarly reacted with 2, 4-di-t-amylphenoxyacetyl chloride. Similarly, 2, 4-di-n-amylphenoxy acetyl chloride is reacted with 1-n-hexyl- or 1-n-dodecyl-3-amino-5-pyrazolone, and m-(2, 4-di-n-amylphenoxy) acetamido benzoyl chloride is reacted with 1-n-dodecyl-3-amino-5-pyrazolone. 1-Methyl (or 1-n-hexyl)-3-(4-aminophenoxy acetamido)-5-pyrazolone is prepared by refluxing 1-methyl (or 1-n-hexyl)-3-amino-5- pyrazolone with p-nitrophenoxy acetyl chloride in acetonitrile and reducing the nitro compound to the amino compound with hydrogen under pressure and a nickel catalyst. Similarly, 1-methyl-3-amino-5-pyrazolone is reacted with g (p-nitrophenoxy) butyryl chloride and the nitro group then reduced to amino. 1-n-Hexyl (or 1-n-dodecyl)-3-amino-5-pyrazolone is prepared by reacting 1-n-hexyl (or 1-n-dodecyl) hydrazine with ethyl b -ethoxy-b -aminoacrylate. 1-n-Dodecyl hydrazine is prepared by refluxing 1-chloro-n-dodecane with aqueous hydrazine in ethyl alcohol. g -(p-Nitrophenoxy) butyryl chloride is prepared by reacting p-nitrophenol with g -chlorobutyronitrile, hydrolysing the resulting nitrile to the butyric acid with glacial acetic acid and conc, hydrochloric acid, and converting the acid to its chloride with thionyl chloride. m-(2, 4-Di-n-amylphenoxy) acetamidobenzoyl chloride is prepared by acylating m-aminobenzoic acid with a (2, 4-di-n-amylphenoxy) acetyl chloride and converting the acid to the acid chloride with thionyl chloride. Specifications 524,154, 524,554, 524,559, 536,577, 541,589, 547,064, 599,919, 680,474, 758,165 and 800,108 are referred to.