Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 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 C25H47NO8, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.
van Alphen, J. published the artcileThe reaction between α-halogen ketones and derivatives of phenylhydrazine. I. The reactivity of the N:NC:C group in α-phenylazocrotonic acid esters, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1945), 109-14, database is CAplus.
α-Phenylazocrotonic acid (I) Et ester, prepared from 16.5 g. ClCH2CO2Et (II) in 60 ml. EtOH mixed with cooling with 10.8 g. PhNHNH2 in 100 ml. EtOH and 13.6 g. crystallized NaOAc in 30 ml. H2O, seps. as red needles, m. 51°. After a long time 1-phenyl-3-methyl-4-phenylazo-5-pyrazolone (III), m. 158°, seps. from the mother liquor. I Me ester, prepared in the same manner, m. 46° (from EtOH). When the Et ester was ozonized in CHCl3 at 0°, then decomposed with ice and CaCO3, the CHCl3 layer contained an oil which was reduced in EtOH with Al-Hg, yielding PhNHNHAc, thus proving the structure of I. Reduction of I (Raney Ni, H) yielded 4,4′-bi[1-phenyl-3-methylpyrazolone] (IV), which, boiled with FeCl3, gave the characteristic blue color of “pyrazolone blue” in CHCl3. I reduced in EtOH (Al-Hg) yielded 1-phenyl-3-methyl-5-pyrazolone (V). Bromination of I yielded tars. Bromination in small amounts in Et2O yielded 1-(4-bromophenyl)-3-methyl-4-bromo-5-pyrazolone, m. 171°. Me ester of I yielded the same product. Et ester of I reacted in dry Et2O with HCl to give a salt which, boiled with H2O, yielded 1-phenyl-3-methyl-4-chloro-5-pyrazolone (VI), m. 153°. Me ester of I yielded the same product. Heating VI with PhNHNH2 yielded III. That the Cl had not entered the ring was shown by the preparation of 1-(4-chlorophenyl)-3-methyl-5-pyrazolone, m. 168°, and 1-(2-chlorophenyl)-3-methyl-5-pyrazolone, m. 109°. Et acetoacetate p-chlorphenylhydrazone, yellow needles, m. 111°. PhMgBr added to I gave a complex mixture of unidentifiable products. I does not add to maleic anhydride.
Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 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 C25H47NO8, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics