Patent GB-680488-A (GB)
Title: Improvements in colour photographic couplers
IPC: G03C7/384
Filed: 1950-06-07
Abstract: 1 - (21 : 41 : 61 - Tribromophenyl) - 3 - benzamido-5-pyrazolone is prepared by heating together 1 - (21 : 41 : 61 - tribromophenyl) - 3 - amino-5-pyrazolone and benzoyl chloride in pyridine to form the dibenzoyl derivative, and partially saponifying in alcoholic potassium hydroxide.  1 - (21 : 41 : 61 - Trichlorophenyl) - 3 - benzamido - 5 - pyrazolone, 1 - (21 : 41 : 61 - trichlorophenyl) - 3 - phenylacetamido - 5 - pyrazolone, 1 - (21 : 41 : 61 - tribromophenyl) - 3 - phenylacetamido - 5 - pyrazolone, 1 - (21 : 41 : 61 - trichlorophenyl) - 3 - [b  - (2111 : 4111 - di - tert. - amylphenoxy) - propionamido] - 5 - pyrazolone, 1-(21 : 41 : 61-tribromophenyl)-3-[b -(2111\h : 4111-di-tert. - amylphenoxy) - propionamido] - 5 - pyrazolone, 1 - (21 : 51 - dichloro) - 3 - [311 - (4111 - tert. - amylphenoxy) - benzamido] - 5 - pyrazolone, and 1 - (21 : 41 : 61 - tribromophenyl) - 3 - [311 - (4111 - tert. - amylphenoxy) - benzamido] - 5 - pyrazolone are similarly prepared.  1 - (21 : 41 : 61 - Tribromophenyl) - 3 - amino - 5-pyrazolone is prepared by refluxing together ethyl 2 : 4 : 6 - tribromophenylhydrazine - b  - iminopropionate and sodium ethoxide, and acidifying with glacial acetic acid.  1-(21 : 41 : 61-Trichlorophenyl) - 3 - amino - 5 - pyrazolone, 1 - (21 : 41 - dichlorophenyl) - 3 - amino - 5 - pyrazolone, and 1-(21 : 51-dichlorophenyl)-3-amino-5-pyrazolone are similarly prepared. Ethyl 2 : 4 : 6 - tribromophenylhydrazine - b  - iminopropionate is prepared by refluxing together ethyl b  - ethoxy : b  - iminopropionate and 2 : 4 : 6 - tribromophenylhydrazine in chlorobenzene containing glacial acetic acid.  Ethyl 2 : 4 : 6 - trichlorophenylhydrazine - b  - iminopropionate, ethyl 2 : 4 - dichlorophenylhydrazine - b  - iminopropionate, and ethyl 2 : 5-dichlorophenylhydrazine - b  - iminopropionate are similarly prepared.  2 : 4 : 6 - Tribromophenylhydrazine is prepared by adding diazotized 2 : 4 : 6 - tribromoaniline to cold sodium sulphite solution, warming, and acidifying with concentrated hydrochloric acid.  2 : 4 : 6-Trichlorophenylhydrazine, 2 : 4 - dichlorophenylhydrazine, and 2 : 5 - dichlorophenylhydrazine are similarly prepared.  1 - (21 : 41 - Dichlorophenyl) - 3 - m - nitrobenzamido - 5 - pyrazolone is prepared by refluxing together 1-(21 : 41-dichlorophenyl)-3-amino-5-pyrazolone and m-nitrobenzoyl chloride in glacial acetic acid, and adding caustic solution to an ethanol suspension of the diacyl derivative formed.  1 - (21 : 41 : 61 - Trichlorophenyl) - - m - nitrobenzamido - 5 - pyrazolone, 1 - (21 : 51 - dichlorophenyl)-3-m-nitrobenzamido-5-pyrazolone, and 1 - (21 : 41 : 61 - tribromophenyl) - 3 - m - nitrobenzamido-5-pyrazolone are similarly prepared.  1 - (21 : 41 - Dichlorophenyl) - 3 - (31 - amino - benzamido) - 5 - pyrazolone is prepared by reducing 1 - (21 : 41 - dichlorophenyl) - 3 - (31 - nitrobenzamido)-5-pyrazolone with iron and acetic acid.  1 - (21 : 41 : 61 - Trichlorophenyl)-3-(31 - aminobenzamido) - 5 - pyrazolone, 1-(21 : 51-dichlorophenyl) - 3 - (31 - aminobenzamido) - 5 - pyrazolone and 1-(21 : 41 : 61-tribromophenyl)-3-(31-aminobenzamido)-5-pyrazolone are similarly prepared.  2 - (21 : 41 - Dichlorophenyl) - 3 - [311 - (2111 : 4111-di - tert. - amylphenoxyacetamido) - benzamido]-5-pyrazolone is prepared by reacting 1-(21 : 41-dichlorophenyl) - 3 - (31 - aminobenzamido) - 5 - pyrazolone with 2 : 4 - di - tert. - amylphenoxy - acetyl chloride.  1 - (21 : 51 - Dichlorophenyl) - 3 - [311 - (2111 : 4111 - di - tert. - amylphenoxyacetamido) - benzamido] - 5 - pyrazolone, 1 - (21 : 41 : 61-trichlorophenyl) - 3 - [311 - (2111 : 4111 - di - tert. - amylphenoxyacetamido) - benzamido] - 5 - pyrazolone and the corresponding 21 : 41 : 51-trichlorophenyl compound, and 1-(21 : 41 : 61-tribromophenyl) - 3 - [311 - (2111 : 4111 - di - tert. - amyl - phenoxyacetamido) - benzamido] - 5 - pyrazolone are similarly prepared.  Specifications 524,154, 524,554, 524,555, 541,589, [all in Group XX] 547,064, 599,919 and 680,474 are referred to.