Patent GB-737692-A (GB)
Title: New colour couplers for use in colour photography
Inventor: GREENHALGH COLIN WILLIAM
IPC: C07D231/52
Filed: 1953-02-13
Abstract: 1 - p - Sulphophenyl - 3 - n - octadecylamino-4 - p - (b  : b 1 - dicyanodiethylamino) - benzylidene-5-pyrazolone is prepared by heating together 1 - p - sulphophenyl - 3 - n - octadecylamino - 5 - pyrazolone and p - (b  : b 1 - dicyanodiethylamino)-benzaldehyde in acetic acid.  1 - p - Sulphophenyl - 3 - n - octadecylamino - 4-p - (N - methyl : N - b  - sulphoethylamino)-benzylidene - 5 - pyrazolone, and 1 - p - sulphophenyl - 3 - octadecylamino - 4 - (2 : 4 - dimethoxy) - benzylidene - 5 - pyrazolone are similarly prepared.ALSO:Compounds of the general formula <FORM:0737692/IV (b)/1> wherein X is an aryl radical and Y is an alkyl, aralkyl or cycloalkyl radical, are prepared by treating a 1-aryl-3-amino-5-pyrazolone with a primary amine NH2-Y, e.g. by heating together in a diluent such as acetic acid or 2-ethoxyethanol. The 1-aryl-3-amino-5-pyrazolone may be 1 - phenyl - 3 - amino - 5 - pyrazolone or a derivative thereof containing one or more substituents, e.g. nitro, alkyl, alkoxy or cyano groups or halogen atoms in the phenyl nucleus, and the primary amine may be methyl-, butyl-, benzyl-, cyclohexyl-, dodecyl- or octadecylamine, a hydroxyamine such as b -hydroxyethylamine, or a diamine such as ethylenediamine. When a carboxylic acid is used as the diluent, the hydroxy group or second amino group may be acylated in the reaction. A hydroxy group in the aryl nucleus may be similarly acylated.  A nitro group may be reduced and acylated, e.g. to introduce the octadecenylsuccinyl group, or the aryl group may be sulphonated and a sulphate ester of the enol form of the pyrazolone may be simultaneously formed.  1 - Phenol - 3 - benzylamino - 5 - pyrazolone is prepared by boiling together 1-phenyl-3-amino-5-pyrazolone, benzylamine, and acetic acid. 1-Phenyl-3-n-butylamino-5-pyrazolone, 1-phenyl - 3 - methylamino - 5 - pyrazolone, 1-phenyl - 3 - cyclohexylamino - 5 - pyrazolone, 1-p - nitrophenyl - 3 - benzylamino - 5 - pyrazolone, 1 - phenyl - 3 - b  - acetoxyethylamino - 5 - pyrazolone, 1 - phenyl - 3 - b  - acetaminoethylamino - 5-pyrazolone, 1 - phenyl - 3 - n - octadecylamino - 5-pyrazolone and 1 - [41 - (411 - chlorophenoxy)-phenyl] - 3 - n - octadecylamino - 5 - pyrazolone are similarly prepared.  1 - P - Aminophenyl - 3 - benzylamino - 5-pyrazolone is prepared by reducing 1-p-nitrophenyl - 3 - benzylamino - 5 - pyrazolone with zinc and acetic acid.  1 - P - Octadecenylsuccinaminophenyl - 3-benzylamino - 5 - pyrazolone is prepared by heating together 1 - p - aminophenyl - 3-benzylamino - 5 - pyrazolone, octadecenylsuccinic anhydride, and acetic acid.  1 - Phenyl - 3 - b  - hydroxyethylamino - 5-pyrazolone is prepared by boiling together 1-phenyl - 3 - b  - acetoxyethylamino - 5 - pyrazolone and aqueous sodium hydroxide and acidifying.  1 - P - Sulphophenyl - 3 - n - octadecylamino - 5-pyrazolone is prepared by sulphonating 1-phenyl - 3 - n - octadecylamino - 5 - pyrazolone with 80 per cent sulphuric acid at 120 DEG  C. Sulphonation with 20 per cent oleum at 0 DEG  C. followed by treatment with a methanol solution of sodium acetate yields the disodium salt of 1-p - sulphophenyl - 3 - n - octadecylamino - 5-sulphatopyrazole. Specifications 651,059, [Group XX], and 673,091 are referred to.