Verfahren zur Herstellung von Farbenphotographien

Specified substituted 5-pyrazolones are prepared by reacting specified acyl-carboxylic acid ethyl esters of the type R1CO-CH(R2).CO2C2H5 with certain substituted hydrazines of the type NH2.NH.R3. In these reactions, R1 (which becomes the group in the 3-position of the pyrazolone) is methyl, heptadecyl, phenyl, benzyl or carbethoxy (which may be hydrolysed to carboxy), R2 (in the 4-position) is methyl, ethyl, phenyl or p-chlorophenyl, and R3 (in the 1-position) is phenyl, 2-, 3- or 4-sulphophenyl, 2 - chloro - 4 - sulphophenyl, 3 - nitrophenyl, 2 - ethoxyphenyl, a - pyridyl, a - (4 - methyl-quinolyl), 2-benzthiazolyl or tetramethylene-1 : 4-sulphone. 3-Methyl - 1 - phenyl - 5 - pyrazolone - 4 - iso-butyric acid is prepared by hydrogenation of a mixture of 3-methyl-1-phenyl-5-pyrazolone and ethyl acetoacetate with a nickel catalyst, followed by hydrolysis of the ester group. 3 - Heptadecyl - 4 - isopropyl - 1 - (41 - sulpho-phenyl)-5-pyrazolone is prepared by hydrogenating 3 - heptadecyl - 1 - (41 - sulphophenyl) - 5 - pyrazolone with excess acetone in the presence of a nickel catalyst. 3 - Amino - 4 - isopropyl-1-phenyl-5-pyrazolone is similarly prepared and the 3-amino group converted to a 3-acetylamino-group. 3:4 - Dimethyl - 5 - pyrazolone - 1 - carboxylic acid amide is prepared by reacting a -methyl-acetoacetic acid ethyl ester with aminoguanidine hydrogen carbonate in methanol and glacial acetic acid. 3,3 - 11,21 - Cyclohexenyl - 1 - phenyl - 5 - pyra-zolone is prepared by boiling 1-cyclohexanone-2-carboxylic acid ethyl ester with phenylhydrazine in toluene. 3 - Methyl - 4 - phenyl (or methyl) 1 - (3-aminophenyl)-5-pyrazolone is prepared by reduction from the corresponding 3-nitrophenyl compound, and is then reacted with a -octadecenyl-succinic acid anhydride in glacial acetic acid to give 3-methyl-4-phenyl (or methyl) 1-(31-a - octadecenylsuccinamino - phenyl) - 5 - pyrazolone. 3 - Phenyl - 4 - methyl - 1 - (31 - a - octadecenylsuccinamino - phenyl) - 5 - pyrazolone is similarly prepared. a - (4 - Methyl - quinolyl) hydrazine is prepared by refluxing 2-chloro-4-methyl-quinoline with hydrazine hydrate. N - (tetramethylene - sulphone - 1 : 4) hydrazine is obtained by reacting hydrazine hydrate with butadiene sulphone. a -Methyl-a -stearoyl-acetic acid ethyl ester is prepared by boiling sodium in ethanol with stearoy-acetic acid ethyl ester and then adding methyl iodide. By using ethyl iodide instead of methyl iodide, a -ethyl-a -stearoyl-acetic acid eth