Patent GB-865721-A (GB)
Title: Improvements in and relating to photographic colour development and photographic emulsions containing colour couplers
IPC: G03C7/384
Filed: 1957-10-17
Abstract: 1- (b -Hydroxyethyl)-3- [a -(p-palmitamidophenoxy) acetamido]-5-pyrazolone is prepared by refluxing the corresponding 3-[a -(aminophenoxy) acetamido]-5-pyrazolone in acetonitrile with palmitoyl chloride in the presence of N; p  N-dimethylaniline, and hydrolysing the triacylated product with aqueous sodium or potassium hydroxide followed by acidification with acetic acid.  The corresponding 3-[a -(2; 4-di-t (or n) amylphenoxy) acetamido]-, 3-palmitamido-, and 3-tetracosanamido-5-pyrazolones are similarly obtained from 1-(b -hydroxyethyl)-3-amino-5-pyrazolone by treatment with a -(2; 4-di-t (or n)- amylphenoxy) acetyl chloride, palmitoyl chloride or tetracosyl chloride respectively.  1-[b - 2; 4- Di-n (or t)- amylphenoxyacetoxy) ethyl]-3-(2; 4-di-n (or t)- amylphenoxyacetamido)-5-(2; 4-di-n (or t)- amylphenoxy acetoxy)- pyrazole is prepared by refluxing 1-(b -hydroxyethyl)-3-amino-5-pyrazolone in acetonitrile with 2; 4-di-n- (or t)-amylphenoxyacetyl chloride in the presence of N; N-dimethyl anilide.  Hydrolysis of the product with 2 equivalents of sodium hydroxide in aqueous ethanol gives 1-(b -hydroxyethyl)-3-(2; 4-di-n-amylphenoxyacetamido)-5-pyrazolone.  1-(b -Octanoloxyethyl)-3-(2; 4-di-n-amylphenoxyacetamido)-5-(octanoyloxy) pyrazole is prepared by acylating the corresponding 1-(b -hydroxymethyl)-3-substituted-5-pyrazolone with 2 equivalents of octanoyl chloride.  1, 5-diacylated pyrazoles are similarly made from 1-(b -hydroxyethyl)-3-(21, 4-di-n-amylphenoxyacetamido)-5-pyrazolone using phenylacetyl chloride or phenoxyacetyl chloride as the acylating agent.  1-(b -Hydroxyethyl)-3-)p-[m-(2; 4-di-t-amylphenoxy-acetamido) benzamido] phenoxy-acetamido(-5-pyrazolone is obtained by treating 1-(b -hydroxyethyl)-3-(p-nitro-phenoxyacetamido)-5-pyrazolone with benzoyl chloride to give a dibenzoyl derivative, reducing the nitro group with hydrogen under pressure and palladium on charcoal catalyst, acylating the product with m-2; 4-di-t-amylphenoxyacetamido) benzoyl chloride, and hydrolysing the triacylated compound with sodium hydroxide as above to remove the benzoyl groups.  1-(b -Phenyl (or methyl)- b -hydroxyethyl)-3-(p-nitro phenoxy acetamido)-5-pyrazolone is prepared by treating 1-(b -phenyl (or methyl)-b -hydroxyethyl)-3-amino-5-pyrazolone with one equivalent of p-nitrophenoxyacetyl chloride in acetonitrile. 1-(b -hydroxymethyl)-3-amino-5-pyrazolone may be similarly treated.  The products may be reduced to the amino compounds with hydrogen under pressure, and the amino compound obtained from the 1-(b -methyl-b - hydroxyethyl)-3- substituted-5-pyrazolone may subsequently be reacted with 2; 4-dit-amylphenoxy-acetyl chloride to give 1-(b -hydroxypropyl)-3-[4-(2; 4-di-t-amylphenoxyacetamido) phenoxyacetamido]-5-pyrazolone.  1- (b - Benzoyloxyethyl)-3- benzamido-5-pyrazolone is prepared by acylating 1-(b -hydroxyethyl)-3-amino-5-pyrazolone with benzoyl chloride and hydrolysing the product with sodium hydroxide.  1-(b -Hydroxyethyl)-3- (p-nitrobenzamido)-5-pyrazolone is prepared by acylating 1-(b -hydroxyethyl)-3-amino-5-pyrazolone with 2-nitrobenzoyl chloride and hydrolysing the product with sodium hydroxide.  1-(b -Hydroxyethyl)-3-amino-5-pyrazolone is prepared by mixing b -hydroxyethylhydrabine and ethyl-b -ethoxy-b -iminopropionate in acetic acid.  The corresponding 1-(b -phenyl (or methyl)-b -hydroxyethyl)-3-amino-5-pyrazolones are similarly prepared from b -phenyl (or methyl)-b -hydroxyethylhydrazine. Specifications 524,154, 524,554, 524,555, 536,577, 541,589, 649,660, 680,488, 843,497 and 865,720 are referred to.