Koike, Eiji published the artcileOrganic pigments. II. Syntheses of 1-phenyl-3-methyl-5-pyrazolone and its derivatives, Application In Synthesis of 14580-22-4, the publication is Nippon Kagaku Kaishi (1921-47) (1954), 56-8, database is CAplus.
cf. C.A. 48, 6388d, 11079a. Phenylhydrazine (I) (24 g.) was added within 30 min. to a mixture of 12 g. 60% EtOH and 29.2 g. AcCH2CO2Et (II) below 50掳, stirred for 2 hrs., then refluxed 4 hrs. and filtered to yield 35.5 g. of 1-phenyl-3-methyl-5-pyrazolone, m. 125.0-126.5掳. The treatment of 6.5 g. p-ClC6H4NHNH2.HCl in H2O, acidified with AcOH with 4.8 g. II gave 84% 1-(p-chlorophenyl)-3-methyl-5-pyrazolone, m. 165-6掳. Similarly were prepared the following analogs of III (1-substituent, m.p., % yield given): 慰-ClC6H4, 182-3掳, 68.6; m-ClC6H4, 124-5.5掳, 93.6; 慰-MeC6H4, 180-1掳, 26.6; m-MeC6H4, 104.7-5.0掳, 48; p-MeC6H4, 91.5-3.5掳, 43.6; p-MeOC6H4, 122-3掳, 36.7; m-O2NC6H4, 185掳, 68.5; p-O2NC6H4, 220掳, 80; m-HO3SC6H4, 200掳, 90.8. AcCH2CN (42 g.) in 54 cc. H3O and 16 cc. concentrated HCl treated with 54 g. I in 200 cc. H2O and 41 cc. HCl at 35-40掳, and further addition of 30 cc. concentrated HCl at 90掳 gave 62.5 g. of 1-phenyl-3-methyl-5-aminopyrazole, m. 110-111.5掳.
Nippon Kagaku Kaishi (1921-47) 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, Application In Synthesis of 14580-22-4.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics