Chattaway, F. D. published the artcileHalogen-substituted 1-arylpyrazolones, Related Products of pyrazoles-derivatives, the publication is Journal of the Chemical Society, Transactions (1924), 2423-7, database is CAplus.
The 1-chlorophenyl-3-methyl-5-pyrazolones are very similar in properties to the unsubstituted base, neither the position of the substituted halogen nor its accumulation in the Ph residue appearing greatly to affect the reactivity of the CH2 group. 1-o-Chlorophenyl-3-methyl-5-pyrazoline (I), m. 199°, results by heating MeC(:NNHC6H4Cl)CH2CO2Et at 150-70° for about 90 mins.; HCl salt, m. 154°, decomposes 172°; 4-oximino derivative, golden brown, m. 174°; 4-benzylidene derivative, orange, m. 159°; 4-azo-o-chlorobenzene derivative, golden yellow, m. 212°. I, heated with MeI in MeOH in a sealed tube at 100-20° for 10 hrs., gives the 2,3-di-Me derivative (o-chloroantipyrine), m. 113°, whose aqueous solution has a strong bitter taste. 1-m-Chloro derivative (II), m. 131°; HCl salt, m. 184° (decomposition); 4-oximino derivative, orange, m. 173° (decomposition); 4-benzylidene derivative, red, m. 128°; 4-azo-2′,4′-dichlorobenzene, golden brown, m. 190°; II, heated with Me2CO 4 hrs., gives the 4-isopropylidene derivative, S-yellow, m. 110°; 2,3-di-Me derivative (m-chloroantipyrine), m. 89-90°; its aqueous solution has an extremely bitter taste. II, heated with PhNHNH2 until NH3 is no longer liberated, and NaNO2 in NaOH, added to an excess of dilute H2SO4, give m-chloropyrazole-blue, C20H14O2N4Cl2, dark blue, m. 209° (decomposition); this also results by boiling II with FeCl3; the other Cl derivatives do not show this reaction. It is easily reduced to the bispyrazolone. 1-p-Chloro HCl salt, m. 194-5° (decomposition); 4-oximino derivative, orange needles, m. 180° (decomposition); it also exists as the unstable form, brick-red, compact triclinic prisms; 4-benzylidene derivative, scarlet, m. 156°; 4-azo-p-chlorobenzene, orange-red, m. 232°; 2, 3-di-Me derivative (p-chloroantipyrine), m. 126°; this also has a very bitter taste. Bis-1-chlorophenyl-3-methyl-5-pyrazolone, decomposes without melting; p-chloropyrazole-blue, blue, decomposed at about 300°. 1,2,4-Dichlorophenyl-3-methyl-5-pyrazolone, m. 178°; HCl salt, m. 153°, decomposes 170°; 4-oximino derivative, canary-yellow, m. 166-8° (decomposition); 4-benzylidene derivative, orange, m. 131°; 4-azobenzene derivative, orange, m. 137-8°; 2, 3-di-Me derivative, m. 143°; the aqueous solution has a bitter taste.
Journal of the Chemical Society, Transactions published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Related Products of pyrazoles-derivatives.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics