Patent GB-861138-A (GB)
Title: Colour photography
IPC: G03C7/32
Filed: 1957-09-17
Abstract: 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 ethyl ester is produced.  a -Methyl-acetoacetic acid anilide is prepared by adding aniline to a -methyl-acetoacetic acid ethyl ester in xylene heated on an oil bath. 1-Cyclohexanone-2-oxalic acid anilide is prepared by reacting 1-cyclohexanone-2-oxalic acid ethyl ester with aniline.  If, instead of aniline, 3-aminobenzene sulphonic acid is used, 1-cyclo-hexanone - 2 - oxalic acid - (31 - sulphonamido-anilide) is formed.  1 - Cyclopentanone - 2 - carboxylic acid - (31-sulpho - 41 - N - methyl - heptadecylamino anilide) is obtained by refluxing 4-amino-N-methyl-heptadecylaniline-2-sulphonic acid with cyclopentanone-2-carboxylic acid ethyl ester in toluene. Specifications 458,400, 479,838, 489,162, 489,274, 524,555, 599,377, 617,247 and 795,476 are referred to.