Patent GB-1282486-A (GB)
Title: Improvements in or relating to light-sensitive silver halide colour photographic materials
Inventor: ALTAVILLA ALEX PETER
IPC: G03C7/34
Filed: 1969-07-29
Abstract: 1282486 1-Hydroxy-2-naphthanilide derivatives and intermediates therefor GAF CORP 29 July 1969 [2 Aug 1968] 38111/69 Heading C2C [Also in Division G2] 4 - (N - methyl - N - tetradecyl) - amino - 3- nitro-cinnamic acid is prepared by refluxing a solution comprising 3-nitro-4-chlorocinnamic acid, N-tetradecyl-N-methylamine, triethylamine and dry xylene. 3-amino-4-(N-methyl-N- tetradecyl)-amino-cinnamic acid (compound I) is prepared by treating an ethanolic alkaline solution of the above product with a solution comprising water, sodium hydroxide and sodium thiosulphate. 2<SP>1</SP>-(N-methyl-N-tetradecyl)-amino- 51 - (# - carboxyethylenyl) - 1 - hydroxy - 2- naphthanilide is prepared by heating under vacuum a solution of the above product and "salol" (phenylsalicylate) - 2<SP>1</SP>-(N-methyl-N-tetradecyl) - amino - 5<SP>1</SP>- (# - carboxyethyl) - 1- hydroxy-2-naphthanilide (compound II) is prepared by hydrogenation of the above product. 2<SP>1 </SP>- (N - methyl - N - tetradecyl) - amino - 5<SP>1</SP> - (#- carboxyethyl) - 1 - hydroxy - 2 - naphthanilide - 4- sulphonic acid is prepared by treating compound II above with concentrated sulphuric acid. 2<SP>1</SP>- (N - methyl - N - tetradecyl) - amino - 51 - (#- bromo - # - carboxyethyl) - 1 - hydroxy - 4 - bromo- 2-naphthanilide is prepared by treating compound II above with bromine and glacial acetic acid. 2-(N-methyl-N-tetradecyl)-amino-5-nitrocinnamic acid is prepared by refluxing a solution comprising 2-chloro-5-nitro cinnamic acid, N- methyl-N-tetradecylamine, triethylamine and dimethylsulphoxide. 3<SP>1</SP>-(#-carboxyethyl)-4<SP>1</SP>-[(N- methyl-N-tetradecyl)-amino]-1-hydroxy-2-naphthanilide is prepared by refluxing a solution comprising the above product, absolute ethyl alcohol and concentrated sulphuric acid. α-(p-Carboxyphenyl) - # - (4 - hydroxy - 3 - nitrophenyl) - acrylic acid is prepared by heating a solution comprising homoterephthalic acid, 3-nitro-4-hydroxybenzaldehyde, pyridine and acetic anhydride. α-(p- Carboxyphenyl) - # - (3 - nitro - 4 - tetradecyloxyphenyl)-acrylic acid is prepared by treating the above product with sodium methoxide, tetradecyl bromide, absolute ethanol and dimethyl sulphoxide. α-(#-Carboxyphenyl)-#-(3-amino-4- tetradecyloxyphenyl)-acrylic acid is prepared similarly to compound I above. 2<SP>1</SP>-Tetradecyloxy- 51 - [# - carboxy - # - (411 - carboxyphenyl)- ethylenyl]-1-hydroxy-2-naphthanilide is prepared by heating the above compound with phenyl 1- hydroxy-2-naphthoate. 2<SP>1</SP>-Tetradecyloxy-5<SP>1</SP>-[#- carboxy - # - (p - carboxyphenyl) - ethyl] - 1- hydroxy-2-naphthanilide is prepared by hydrogenation of the above compound. Ethyl 4-nitro- 3-pentadecylphenoxyacetate is prepared by reflexing a solution comprising sodium metal, 3- pentadecyl-4-nitro-phenol, ethyl chloroacetate, dimethyl formamide and absolute alcohol. Ethyl 4-amino-3-pentadecylphenoxyacetate is prepared by hydrogenation of the above compound. 41 - Ethoxycarbonylmethoxy - 1 - hydroxy - 2<SP>1</SP>- pentadecyl-2-naphthanilide is prepared by heating under vacuum the above compound with salol (phenylsalicylate). 4<SP>1</SP>-Carboxymethoxy-1- hydroxy-2<SP>1</SP>-pentadecyl-2-naphthanilide is prepared by alkaline hydrolysis of the above compound. Methyl p-nitrophenoxybutyrate is prepared by refluxing p-nitrophenol, sodium metal and absolute alcohol, diluting with dimethylformamide, adding methyl 4-chlorobutyrate with sodium iodide and refluxing. p-Nitrophenoxybutyric acid is prepared by the alkaline hydrolysis of the above compound. p-Nitrophenoxybutyryl chloride is prepared by treating the above compound with thionyl chloride. 3<SP>1</SP>,5<SP>1</SP>-Bis-(methoxycarbonyl) - 4 - p - nitrophenoxy - N - octadecylbutyranilide is prepared by treating the above product with dimethyl 5-octa-decylamino-isophthalate and dry pyridine. 4-p-Amino-phenoxy - 3<SP>1</SP>,5<SP>1</SP> - bis - (methoxycarbonyl) - N - octadecylbutyranilide is prepared by hydrogenation of the above compound. 1-Hydroxy-4<SP>1</SP>-{3-[N- (3,5 - dimethoxycarbonylphenyl)- N - octadecylcarbamoyl]propyloxy}-2-naphthanilide is prepared by heating under reduced pressure the above product with salol (phenylsalicylate). 4<SP>1</SP>- {3 - [N - (3,5 - dicarboxyphenyl) - N - octadecylcarbamoyl]propyloxy} - 1 - hydroxy - 2 - naphthanilide is prepared by the alkaline hydrolysis of the above compound. 3<SP>1</SP>,5<SP>1</SP>-Bismethoxycarbonyl-2- (2-nitrophenoxy)-N-octadecylacetanilide is prepared by heating o-nitrophenoxyacetylchloride and dimethyl 5-N-octadecylamino-isophthalate. 3<SP>1</SP>,5<SP>1</SP> - Bismethoxycarbonyl - 2 - (2 - aminophenoxy)-N-octadecylacetanilide is prepared by hydrogenation of the above product. 21-[N- (3,5 - bismethoxycarbonylphenyl)- N - octadecylcarbamoylmethoxy] - 1 - hydroxy - 2 - naphthanilide is prepared by heating under reduced pressure the above product with salol (phenylsalicylate). 2<SP>1</SP>-[N-(3,5-dicarboxyphenyl)-N-octadecylcarbamoylmethoxy]- 1 - hydroxy - 2 - naphthanilide (compound III) is prepared by the alkaline hydrolysis of the above product. 4<SP>1</SP>-[N- (3,5 - dicarboxyphenyl) - N - octadecylcarbamoylmethoxy]-1-hydroxy-2-naphthanilide is prepared by a series of reactions identical to that used to prepare compound III above except that onitrophenoxy acetyl chloride is used as the startingmaterial. #-(3-Acetylamino-4-hydroxyphenyl)- propionic acid is prepared by hydrogenation of 3-acetylamino-4-hydroxycinnamic acid. #-(3- Acetylamino-4-tetradecyloxyphenyl)propionic acid is prepared by refluxing the above product with sodium methoxide, tetradecyl bromide and absolute alcohol. #-(3-Amino-4-tetradecyloxyphenyl)propionic acid is prepared by the alkaline hydrolysis of the above product. 1-Hydroxy-2- [21 - tetradecyloxy - 51 - (# - carboxyethyl)]- naphthanilide is prepared by heating the above product with salol (phenylsalicylate); ethanol and triethylamine.