Fusco, Raffaello published the artcileEnamines. V. Synthesis of 1-arylpyrazoles, Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, the publication is Gazzetta Chimica Italiana (1961), 1233-49, database is CAplus.
cf. CA 56, 14018c. Enamines and halogenated hydrazones reacted to give pyrazole derivatives In anhyd, conditions 16.7 g. 1-morpholinocyclohex-l-ene (I), 10.1 g. NEt3, 150 mL. CHCl3, and 22.6 g. PhNHN: CClCO2Et added in 50 mL. CHCl3 was stirred and heated to 40° for 1 h. and kept overnight to give 65% 1-phenyl-3-carbethoxy-4,5,6,7-tetrahydroindazole (II) m. 103-4.5° (EtOH), hydrolyzed by alc. NaOH to 1-phenyl-4,5,6,7-tetrahydroindazole-3-carboxylic acid, m. 164° (AcOH). Similarly, the p-chlorophenyl compound, m. 139-40°, and its corresponding acid m. 218°. Treatment of I with PhNHN:CClAe gave 1-phenyl-3-acetyl-4,5,6,7-tetrahydroindazole, m. 95-6°; phenylhydrazone m. 216° (dilute AcOH). 1-Morpholino-4-methylcyclohex-1-ene gave the 5-Me deriv, of II, m. 129°, hydrolyzed to the corresponding acid m. 198°. 1-Phenyl-3-carbethoxy-4,5,6,7-tetrahydrocydohepta[c]pyrazole (III), m. 87% was prepared from 1-morpholinocyclohept-1-ene and was hydrolyzed to the corresponding acid, m. 166-8°. The 1-(p-chlorophenyl) compd, corresponding to III could not be isolated and was hydrolyzed to the acid, m. 206-7°. From 2 morpholino-3,4-dihydronaphthalene and PhNHN: CClCO2Et, 1-phenyl-3-carbethoxy-8,9-dihydronaphtho[1,2-c]pyrazole, m. 154-5°, was prepared, giving the acid, m. 170°, on hydrolysis: when decarboxylated at 240°, this gave 1-phenyl-8,9-dihydronaphtho[1,2-c]pyrazole, m. 118°. The compound formed from 1-morpholinocyclopent-1-ene and PhNHN:-CClCO2Et was an intermediate, C19H25N3O3, m. 130° (ale.), converted into the expected 1-phenvl-3-carbethoxy-4,5-dihydrocyclopenta[c] pyrazole, m. 143°. on boiling with AcOH followed by precipitation by addition of water. The corresponding acid, m. 211°; Me ester m. 139°. Similarly the 1-(p-chlorophenyl) compd, gave an adduet, C19H24ClN3O3, m. 114° cyclized to the pyrazole, m. 120-1°, which in turn was hydrolyzed to the corresponding free acid, m. 215-16°. Similarly were prepared 1-phenyl-3-carbethoxyindeno[1,2-c]-pyrazole, m. 162-3° (the acid m. 256°), 1-phenyl-3-carbethoxy-4-ethylpyrazole, m. 70° (free acid m. 138°), 1-phenyl-3-carbethoxy-4-n-amylpyrazole, m. 45-6° (free acid m. 121°), [the corresponding 1-(p-chlorophenyl) compd, m. 62° (free acid m. 115°)]. From 2-N-methyl-N-phenyl-amino-4-methylpent-l-ene, the ester prepd, was an oil, b2 186°, which gave 1-phenyl-5-isobutylpyrazole-3-carboxylic acid, m. 129°, on hydrolysis, α-(N-Methyl-N-phenyl)-aminostyrene and PhNHN:CClCO2Et after reaction, evapn, of solvent, steam distn, to remove PhAe, and hydrolysis gave 1,5-diphenylpyrazole-3-carboxylic acid, m. 183°. 1-Phenyl-3-carbethoxy-4-γ-methylaminoethyl-5-methylpyrazole oxalate, m. 174-5° (iso-PrOH), was prepared from 1,2-dimethyl-4,5-dihydropyrrole and gave the corresponding base, as a straw-colored oil, b1.5 220-40°, which on hydrolysis with 40% HBr gave the free carboxylic acid of the base after addition of Ag2O to precipitate AgBr, filtration, and passage of H2S to decomp, the Ag salt; the filtrate evaporated to dryness and the solid washed with MeOH and recrystallized from water gave the acid, m. 297°. 1-Phenyl-3-carbethoxy-4-γ-methylaminopropyl-5-methylpyrazole-HCl, m. 186-7° (iso-PrOH), 1-phenyl-4-γ-methylaminopropyl-5-methylpyrazolecarboxylic acid, m. 270-1° (5% aqueous EtCO-Me), and 1-phenyl-3-acetyl-4-γ-methylaminopropyl-5-methylpyrazole oxalate, m. 17,5-6°, were also prepared
Gazzetta Chimica Italiana published new progress about 13599-22-9. 13599-22-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid,Benzene, name is 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, and the molecular formula is C16H12N2O2, Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid.
Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics