DIFFUSION RESISTANT DISPERSIBLE MAGENTA COUPLERS FOR PRODUCING COLOURED PHOTOGRAPHIC IMAGES

摘要

1448948 3 - Anilino - pyrazol - 5 - ones and intermediates therefor AGFA-GEVAERT AG 18 July 1974 [18 July 1973] 31800/74 Heading C2C [Also in Division G2] 2,6 - Dichloro - 4 - methoxyaniline is prepared by adding 4-nitrosophenol at 15-20‹ C. into a saturated solution of hydrogen chloride in methanol, introducing further hydrogen chloride, cooling to 10‹ C., filtering, washing with methanol, filtering, boiling the residue with methanol and stirring into water to precipitate the product. 2,6 - Dichloro - 4 - methoxyphenylhydrazine is prepared by adding 2,6-dichloro-4- methoxyaniline to concentrated hydrochloric acid, diluting with water, adding aqueous sodium nitrite dropwise at 0-3‹ C., filtering, adding the clear solution dropwise at 0-5‹ C. to SnCl 2 .2H 2 O in concentrated hydrochloric acid, filtering, washing with 5NHCl and water, dissolving the residue in methanol and stirring into aqueous sodium hydroxide to give the product. 1 - (21,61 - Dichloro - 41 - methoxyphenyl) - 3 - (211- chloro-511-nitroanilino)pyrazolone is prepared by adding 2 - chloro - 5 - nitroanilino - # - ethoxyacrylic acid ethyl ester to 2,6-dichloro-4-methoxyphenylhydrazine suspended in glacial acetic acid, filtering, washing with glacial acetic acid, methanol and ether, suspending the residue in absolute methanol, adding 4M sodium methylate solution at 45‹ C., boiling and adding glacial acetic acid to precipitate the product. 1-(21,61- Dichloro - 41 - methoxyphenyl) - 3 - (211 - chloro- 511 - aminoalinino)pyrazolone is prepared by catalytically hydrogenating the above nitro compound. The coupler of the formula is prepared by suspending the above pyrazolone in anhydrous dioxane and pyridine, adding 2- cyclopentyl - 4 - tart. - butyl - phenoxyglycolchlorocarbonic acid ester, stirring the mixture into ice water, acidifying and filtering to give the crude product which is then recrystallized.