Patent GB-1392433-A (GB)
Title: Photographic diffusion transfer methods and recording materials therefor
IPC: G03C8/12
Filed: 1971-03-31
Abstract: 1392433 Quinoline - 6 - sulphonic acid derivatives and intermediates therefor AGFAGEVAERT 27 Match 1972 [31 March 1971 14 Oct 1971] 8338/71 and 47883/71 Heading C2C [Also in Division G2] N - (3,5 - dimethoxycarbonylphenyl) α- benzoylacetamide is prepared by refluxing dimethyl 5-aminoisophthalate and ethyl benzoylacetate in p-xylene. N-(3-methoxy-carbonyl-5- carboxyphenyl) α-benzoylacetamide is prepared by refluxing the above compound in ethanol and aqueous sodium hydroxide and acidifying the filtrate. N - (3,5 - dicarboxyphenyl) α - benzoylacetamide is prepared by similar refluxing and acidifying of the same compound. N-(pfluorosulphonylphenyl) 1 - hydroxy - 2 - naphfhamicle is prepared from p-fluorosulphonylaniline and phenyl α-hydroxy-#-naphthoate. N-(phydrazinosulphonylphenyl) 1 - hydroxy - 2- naphthamide is prepared by treating the corresponding N - (p - fluorosulphonylphenyl) derivative above with hydrazine hydrate in dioxan. 1 - Methyl - 2 - phenyl - 4 - {N - [p- (1 - hydroxy - 2 - naphthamido)phenylsulphonyl]- hydrazono} - 6 - fluorosulphonyldihydroquinoline is prepared by condensing the above sulphonylhydrazide with l-methyl-2-phenyl-6-fluorosulphonyl - 4 - chloro - quinolinium methyl sulphate. 1 - Methyl - 2 - phenyl - 4 - {N - [p- (1 - hydroxy - 2 - naphthamido)phenylsulphonyl]- hydrazono} - 6 - sulphodihydroquinoline is prepared by saponification of the corresponding 6-fluorosulphonyl derivative above. 1-Methyl-2- phenyl - 4 - {N - [p - amino - phenylsulphonyt}- hydrazono} - 6 - fluorosulphonyl - dihydroquinoline is prepared by refluxing acetamidophenylsulphonylhydrazide in chloroform/dry ethanol with 1 - methyl - 2 - phenyl - 4 - chloro - 6- fluorosulphonyl quinolinium methyl sulphate, adding hydrochloric acid in ethanol, refluxing, cooling, separating the hydrochloride, dissolving in the minimum amount of pyridine and pouring into water. 1-Methyl-2-phenyl-4-{N-[p-(α-benzoylacetamido)phenylsulphonyl]- hydrazono} - 6- fluorosulphonyldihydroquinoline is prepared by heating the corresponding p-aminophenylsul phonyl derivative above with ethyl α-benzoylacetate on an oil bath at 100 C. 1-Methyl-2. phenyl - 4 - {N - [p - (α - benzoylacetamido)- phenylsulphonyl]hydrazono} - 6 - sulphodihydroquinoline is prepared by refluxing the 6-fluorosulphonyl derivative above in aqueous sodium hydroxide and acetone. 1-Methyl-2-phenyl-4- {N - [p - (α - cyanoacetamido)phenylsulphonyl]- hydrazono} - 6 - fluorosulphonyldihydroquinoline hydrochloride is prepared by adding 1-cyanoacetyl - 2,4 - dimethyl - pyrazole in acetic acid to the corresponding p-amino-phenylsulphonyl derivative above in acetic acid, stirring, pouring into water, salting out and stirring. 1- Methyl - 2 - phenyl - 4 - {N - [p - (α - cyanoacetamido) - phenylsulphonyl] - hydrazono} - 6 - sulphodihydroquinoline is prepared by adding 1- cyanoacetyl-2,4-dimethylpyrazole in dimethylformamide to 1 - methyl - 2 - phenyl - 4 - {N- [p - aminophenylsulphonyl]hydrazono} - 6- sulphodihydroquinoline in dimethylformamide/triisopropanolamine, stirring, adding more of the pyrazole, stirring, acidifying with hydrochloric acid and pouring into water.