Patent GB-651424-A (GB)
Title: Improvements in colour photographic materials
IPC: G03C7/32
Filed: 1948-02-24
Abstract: 1 - [41 - (o - Terphenyl)] - 3 - amino - 5 - pyrazolone is prepared by refluxing together hydrazino-o - terphenyl and ethyl b  - ethoxy : b  - iminopropionate in ethyl alcohol containing acetic acid, adding sodium ethoxide and refluxing, and acidifying with acetic acid.  1 - [41 - (o - Terphenyl)] - 3 - benzamido - 5 - pyrazolone is prepared by treating 1-[41-(o-terphenyl)] - 3 - amino - 5 - pyrazolone in pyridine with benzoyl chloride.  1 - (p - Cyanophenyl) - 3 - (41 - o - terphenamido) - 5 - pyrazolone is prepared by successively adding o-terphenyl-41-carboxylic acid chloride and quinoline to a dioxane solution of 1-(p-cyanophenyl)-3-amino-5-pyrazolone.  1 - [p - (p1 - tert.-Butylphenoxy) - phenyl] - 3 - 41 - o - terphenamido) - 5 - pyrazolone is prepared by refluxing together 1 - p - (p1 - tert. - butylphenoxy) - phenyl - 3 - amino - 5 - pyrazolone and o-terphenyl-41-carboxylic acid chloride in xylene, and partially saponifying the resulting diacyl compound.  1 - [p - (p1 - tert. - Butylphenoxy) - phenyl] - 3 - (x11 - chlorosulphonyl - 41 - o - terphenamido) - 5 - (x11 - chlorosulphonyl - 41 - o - terphenoxy) - pyrazole is prepared by condensing one mole. of 1 - p - (p1 - tert. - butylphenoxy) - phenyl - 3 - amino - 5 - pyrazolone with two moles. of 41 - carboxy - x11 - sulpho - o - terphenyl dichloride in boiling anhydrous ethyl acetate.  1 - Hydroxy - 2 - [41 - (o - terphenyl)] - naphthamide is prepared by heating together phenyl 1-hydroxy - 2 - naphthoate and 41 - amino - o - terphenyl.  1 - Hydroxy - 2 - }b  - [41 - (411 - o - terphenamido)] - phenethyl} - naphthamide is prepared by condensing 1-hydroxy-2-b -(41-aminophenyl)-ethylnaphthamide hydrochloride and o-terphenyl-41-carboxylic acid chloride in dioxane in presence of quinoline. 1-Hydroxy-2-{b -41-(x11 chlorosulphonyl - 411 - o - terphenamido)] - phenethyl}-naphthamide is similarly prepared.  41 - Benzoylacetamido - o - terphenyl is prepared by heating together ethyl benzoylacetate and 41-amino-o-terphenyl in xylene. 41-(o-Methoxybenzoylacetamido) - o - terphenyl, 4 - benzoylacetamido - m - terphenyl, 41 - benzoylacetamido - p - terphenyl, x - benzoylacetamido) - 2 : 3 : 6 - triphenyltoluene, and x - benzoylacetamido) - 41 - n - butyl - o - terphenyl are similarly prepared.  41-n-Butyryl-o-terphenyl is prepared by adding aluminium chloride to o-terphenyl and n-butyrul chloride in ethylene dichloride.  41-n-Butyl-o-terphenyl is similarly prepared. 41-n-Butyl-o-terphenyl is prepared by refluxing together 41-n-butyryl-o-terphenyl, zinc amalgam, hydrochloric acid, acetic acid, and toluene.  41-Nitro-o-terphenyl is prepared by adding a mixture of fuming and red fuming nitric acids to a hot solution of o-terphenyl in glacial acetic acid.  41 - n - Butyl - x - nitro - o - terphenyl is similarly prepared.  41-Amino-o-terphenyl is prepared by reducing 41 - nitro - o - terphenyl with hydrogen under pressure in presence of Raney nickel.  41-n-Butyl-x-amino-o-terphenyl is similarly prepared.  41-Carboxy-o-terphenyl is prepared by oxidizing 41-acetyl-o-terphenyl in methanol with sodium hypochlorite. 41-Carboxy-x-sulpho-o-terphenyl is prepared by reacting 41-carboxy-o-terphenyl in tetrachlorethane with chlorosulphonic acid. 41 - Carboxy - x - sulpho - o - terphenyl dichloride is prepared by reacting 41-carboxy-x-sulpho-o-terphenyl with PCl5. 41-Hydrazino-o-terphenyl is prepared by diazotizing 41-amino-o-terphenyl and reducing with acid stannous chloride.  4 - (p - tert. - Butylphenoxy) - phenylhydrazine hydrochloride is prepared by diazotizing 4-(p-tert.-butylphenoxy)-aniline with hydrochloric acid and sodium nitrite, adding the mixture obtained to aqueous sodium sulphite, adding hydrochloric acid, raising the temperature to 70 DEG  C., and successively adding acetic acid and zinc dust.  1 - p - (p1 - tert. - Butylphenoxy) - phenyl - 3 - amino - 5 - pyrazolone is prepared by adding 4 - (p - tert. - butylphenoxy) - phenylhydrazine hydrochloride to a boiling solution of ethyl cyanacetate and sodium ethoxide in ethyl alcohol, and refluxing.  1 - Hydroxy - 2 - b  - (41 - aminophenyl) - ethylnaphthamide is prepared by heating together 4 - amino - b  - phenethylamine and phenyl 1-hydroxy-2-naphthoate.