Patent GB-627814-A (GB)
Title: Improvements in colour photographic development and colour-forming developers
IPC: G03C7/333
Filed: 1947-07-10
Abstract: 1 - Hydroxy - 41 - (p-tert. - butylphenoxy) - 2 - naphthanilide is prepared by condensing phenyl 1-hydroxy-2-naphthoate with p-(p-tert.-butylphenoxy)-aniline at 200 DEG  C.  1-Hydroxy-41-2 : 4-diamylphenoxy)-2-naphthanilide is similarly prepared.  1 - Hydroxy - 41 - (p-tert. - amylphenoxy) - 2 - naphthanilide is prepared by condensing 1-hydroxy-2-naphthoyl chloride with p-(p-tert.-amylphenoxy)-aniline. 1-Hydroxy-N-methyl-2-naphthanilide and 1-hydroxy-N-isoamyl-2-naphthanilide are similarly prepared. P-(p-tert.-butylphenoxy)-nitrobenzene is prepared by alkaline condensation of hot p-nitrochlorobenzene and p-tert.-butylphenol. P-(p-tert.-amylphenoxy)-nitrobenzene is similarly prepared. P-(p-tert.-butylphenoxy)-aniline is prepared by catalytic reduction of p-(p-tert.-butylphenoxy) - nitrobenzene with hydrogen in presence of Raney nickel. P-(p-tert.-amylphenoxy)-aniline is similarly prepared.  1 - Hydroxy - N - (p - nitrophenethyl) - 2 - naphthamide is prepared by heating phenyl 1-hydroxynaphthoate with p-nitrophenethylamine.  1 - Hydroxy - N - (p - aminophenethyl) - 2 - naphthamide is prepared by reducing 1-hydroxy-N - (p - nitrophenethyl) - 2 - naphthamide with hydrogen in presence of Raney nickel.  1 - Hydroxy - N - {4 - (2 - (2 : 4 - diamylphenoxy) - 5 - nitrobenzamido) - phenethyl} - 2 - naphthamide is prepared by condensing 1-hydroxy - N - (p - aminophenethyl) - 2 - naphthamide with 2-(2 : 4-diamylphenoxy)-5-mitrobenzoyl chloride in acetic acid containing sodium acetate.  1 - Hydroxy - N - {4 - [2 - (2 : 4 - diamylphenoxy) - 5 - aminobenzamido] - phenethyl} - 2 - naphthamide is prepared by reducing 1-hydroxy-N - {4 - [2 - (2 : 4 - diamylphenoxy) - 5 - nitrobenzamido] - phenethyl} - 2 - naphthamide with hydrogen in presence of Raney nickel.  1 - Hydroxy - N - {4 - [2 - (2 : 4 - diamylphenoxy) - 5 - (3 : 5 - dichlorosulphonylbenzamido) - benzamido] - phenethyl} - 2 - naphthamide is prepared by condensing 1-hydroxy-N-{4-[2-(2 : 4-diamylphenoxy( - 5 - aminobenzamido] - phenethyl} - 2 - naphthamide with 3 : 5 - dichlorosulphonylbenzoyl chloride in dioxane and quinoline.ALSO:1 - Hydroxy - 4 - benzeneazo - 41 - (p - tert.-butylphenoxy) - 2 - naphthanilide is prepared by adding an aqueous solution of benzenediazonium chloride to 1-hydroxy-41-(p-tert.-butylphenoxy)-2-naphthanilide dissolved in a mixture of pyridine and ethanol, and pouring into dilute HCl.  The corresponding 4-o-methoxybenzeneazo -, 4 - p - acetamidobenzeneazo -, 4 - (2 - methoxy - 4 - nitrobenzeneazo)-, and 4 - [(2 - methoxy - 4 - benzeneazo) - benzeneazo] - compounds; 1 - hydroxy - 4 - (o - methoxybenzeneazo) - 41 - (p - tert. - amylphenoxy) - 2-naphthanilide; 1 - hydroxy - 4 - (p - bromobenzeneazo) - 41 - (2 : 4 - diamylphenoxy) - 2-naphthanilide; 1 - hydroxy - 4 - benzeneazo - N-[4 - {2 - (2 : 4 - diamylphenoxy) - 5 - (3 : 5-dichlorosulphonylbenzamido) - benzamido} -phenethyl] - 2 - naphthamide; 1 - hydroxy - 4 - (o-carbethoxybenzeneazo) - N - methyl - 2 - naphthanilide; 1 - hydroxy - 4 - (2 - methoxy - 4 - nitrobenzeneazo) - N - isoamyl - 2 - naphthanilide; and 1 - hydroxy - 4 - [2 - methoxy - 4 - (o-methoxybenzeneazo) - benzeneazo] - N - isoamyl-2-naphthanilide are similarly prepared.