Category: 14580-22-4

Parekh, Nikhil M. published the artcileDyeing performance of heterocyclic monoazo dyes based on 3-amino-1H-pyrazolon[3,4-b]quinoline derivatives on various fibers, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Archives of Applied Science Research (2011), 3(4), 359-365, database is CAplus.

1H-Pyrazolo[3,4-b]quinolin-3-amine derivatives have been synthesized by the reaction between substituted Ph pyrazolones and 3-amino-1H-pyrazolon[3,4-b]quinoline. The novel compound structures have been established on the basis of their substituted Ph pyrazolones derivatives All the azo compounds were characterized by their percentage yield, m.p., elemental anal., UV visible spectra, IR spectra, NMR spectra and dyeing performance on nylon, wool, silk and polyester fibers. All the synthesized dyes gave moderate to excellent fastness properties on each fiber.

Archives of Applied Science Research 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 of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Usui, Yoshiro published the artcileFungicides. XIII. Synthesis and antifungal activity of halogen-substituted phenylhydrazine derivatives and related compounds, Product Details of C10H9ClN2O, the publication is Yakugaku Zasshi (1967), 87(1), 43-65, database is CAplus and MEDLINE.

cf. CA 67: 11452h. Various kinds of halo-substituted phenylhydrazine derivatives and related compounds were synthesized and their bactericidal and fungicidal activities tested. Thus, 3,4-dichlorophenylhydrazine was dissolved in 10 volumes EtOH, equimolar HNO3 added, and the whole solution stirred 1 hr. to give 86% nitrate, m. 182° (decomposition) (EtOH). Similarly the sulfate, brown, m. 198° (decomposition) (H2O), was prepared in 44% yield. Also prepared were the following I (X, R, recrystallization solvent, and m.p. given): 2-Cl, CHO, EtOH, 148-9°; 3,4-di-Cl, CHO, EtOH, 136-7°; 4-Cl, C11H23CO, MeOH, 97-9°; 3,4-di-Cl, EtCO, C6H6, 149-50°; 3,4-di-Cl, PrCO, ligroine, 119-20°; 3,4-di-Cl, BuCO, C6H6, 120-1°; 3,4-di-Cl, AmCO, C6H6, 108-9°; 3,4-di-Cl, C6H13CO, ligroine, 94-5°; 3,4-di-Cl, C7H15CO, MeOH, 92-3°; 3,4-di-Cl, C8H17CO, ligroine, 86-7°; 3,4-di-Cl, C9H19CO, ligroine, 86-7°; 3,4-di-Cl, C11H23CO, ligroine, 84-7°; 3,4-di-Cl, C13H27CO, EtOH, 91-2°; 3,4-di-Cl, C15H31CO, EtOH, 97-8°; 3,4-di-Cl, C17H35CO, EtOH, 90-1°; 3,4-di-Cl, ClCH2CO (yellow), EtOH, 149-50°; 3,4-di-Cl, AcCH2CH2CO, C6H6, 135-6°; 3,4-di-Cl, HO2C(CH2)2CO (gray), H2O, 167-8°; 3,4-di-Cl, HO2C(CH2)4CO, AcOEt-C6H6, 133-5° (decomposition); 3,4-di-Cl, Bz, EtOH, 176-7°; 3,4-di-Cl, 3,4-di-chlorobenzoyl, EtOH, 205-6°; 3,4-di-Cl, 4-nitrobenzoyl (yellow), EtOH, 222-3°; 3,4-di-Cl, 2-hydroxybenzoyl, C6H6, 153-4°; 3,4-di-Cl, 2,4-dichlorophenoxyacetyl, EtOH, 199-200°; 3,4-di-Cl, p-MeC6H4SO2, EtOH, 153° (decomposition); 3,4-di-Cl, PhCH2O2CNHCH(CO2H)CH2CO, EtOH-ligroine, 155-8° (decomposition); 3,4-di-Cl, PhCH2O2CNHCH(CO2H)(CH2)2CO, EtOH-ligroine, 169-70° (decomposition); 3,4-di-Cl, NH2CS (brown) EtOH, 197-8° (decomposition); 2,6-di-Cl, NH2CS, MeOH, 223° (decomposition); 2,3-di-Cl, NH2CS (pale pink) EtOH, 200° (decomposition); 2,4,6-tri-Cl, NH2CS, EtOH, 241 (decomposition); 2,4,5-tri-Cl, NH2CS, EtOH, 226° (decomposition); 3,4-di-Cl, NH2CO (yellow), EtOH, 162-3°; 2,5-di-Cl, NH2CO, EtOH, 224° (decomposition); 4-Cl, MeNHCO, MeOH, 184-5°; 4-Cl, EtNHCO, MeOH, 162-3°; 4-Cl, PhNHCO, MeOH, 192-3°; 4-Cl, p-MeOC6H4NHCO, MeOH, 174-5°; 4-Cl, p-EtOC6H4NHCO, MeOH, 172-3°; 4-Cl, p-AcOC6H4NHCO, MeOH, 175-6°; 4-Cl, PhCH2NHCO, MeOH, 162-3°; 4-Cl, 1-naphthylacrbamoyl, MeOH, 245-6° (decomposition); 4-Cl, 2-ClC6H4NHCO, MeOH, 181-2°; 4-Cl, 3-ClC6H4NHCO, MeOH, 174-5°; 4-Cl, 4-ClC6H4NHCO, MeOH, 213-14°; 3,4-di-Cl, MeNHCO, MeOH, 192-3°; 3,4-di-Cl, EtNHCO, MeOH, 170-1°; 3,4-di-Cl, PhNHCO, MeOH, 202-3°; 3,4-di-Cl, p-OMeC6H4NHCO, MeOH, 192-3°; 3,4-di-Cl, p-EtOC6H4NHCO, MeOH, 207-8°; 3,4-di-Cl, p-AcOC6H4NHCO, MeOH, 221-2°; 3,4-di-Cl, PhCH2NHCO, MeOH, 181.5-2.5°; 3,4-di-Cl, 1-naphthylcarbamoyl, MeOH, 242-3° (decomposition); 3,4-di-Cl, 2-ClC6H4NHCO, C6H6, 195-6°; 3,4-di-Cl, 3-ClC6H4NHCO, C6H6, 203-4°; 3,4-di-Cl, 4-ClC6H4NHCO, C6H6, 205-6°; 2-Cl, EtO2C, ligroine, 78-9°; 4-Cl, EtO2C, ligroine, 88-9°; 2,5-di-Cl, EtO2CO, ligroine, 77-9°; 3,4-di-Cl, EtO2C, ligroine, 108-10°; 2,4-di-Cl, EtO2C (pale yellow), ligroine, 68-9°; 2-Cl, EtS2C (pale green), EtOH, 123-4°; 4-Cl, EtS2C, ligroine, 133-4°; 2,5-di-Cl, EtS2C, ligroine, 145-6°; 3,4-di-Cl, EtS2C (yellow), dilute EtOH, 113-14°; 2,6-di-Cl, EtS2C, ligroine, 128-9°; 4-Cl, BzCH2S2C, EtOH, 177° (decomposition); 3,4-di-Cl, BzCH2S2C (yellow), dilute EtOH, 158-9° (decomposition); 4-Cl, NH2C(:NH) (sulfate), dilute EtOH, 218-19° (decomposition); 3,4-di-Cl, NH2C(:NH) (sulfate), H2O, 235-7° (decomposition); 4-Cl, II (hydriodide) (pale yellow), AcOEt-EtOH, 192-3°; 4-Cl, (OEt)2P(O) (pale yellow), ligroine, 135-6°; 3,4-di-Cl, (OEt)2P(O), ligroine, 105-7°. Also prepared were the following III (X, R, recrystallization solvent, and m.p. given); 4-Cl, C11H23, MeOH, 86-8°; 3,4-di-Cl, C13H27, EtOH, 78-81°; 3,4-di-Cl, C15H31, EtOH, 78-9°; 4-Cl, PhNH, AcOEt, 194-5°. Also prepared was 3,4-Cl2C6H3N(CO2Et)NHAc, [pink, m.99-100° (dilute EtOH)]. Also prepared were the following IV (X, R, recrystallization solvent, and m.p. given): 3,4-di-Cl, 2-nitro-5-furyl (reddish purple), EtOH, 199-200° (decomposition); 4-Cl, HOCH2(CH2OH)4, dilute EtOH, 151-2°; 3,4-di-Cl, HOCH2(CH2OH)4 (gray), dilute EtOH, 168-9° (decomposition). Also prepared were the following V (X, recrystallization solvent, and m.p. given): 2-Cl, EtOH, 231° (decomposition); 3,4-di-Cl, dilute EtOH, 215° (decomposition); 2,4-di-Cl, EtOH, 240° (decomposition); 2,5-di-Cl, AcOEt, 263-4°. Also prepared were the following VI (X, R, color, and m.p. given; all being recrystallized from EtOH): 3,4-di-Cl, 2-hydroxy-1-naphthyl, red, 155-6°; 3,4-di-Cl, 2-HO-5-ClC6H3, dark yellow, 146-8°; 3,4-di-Cl, 2-OH-5-MeC6H4, yellow, 125-6°; 3,4-di-Cl, 2-HO-3-(3,4-Cl2C6H3N:N)-5-MeC6H2, dark yellow, 211-13°; 3,4-di-Cl, 2-HO-5-PhC6H3, dark yellow, 162-3°; 3,4-di-Cl, PhNH, yellow, 93-5°; 3,4-di-Cl, 3-ClC6H4NH, dark yellow, 134-5° (decomposition); 3,4-di-Cl, 2-ClC6H4NH, yellow, 103-4°; 3,4-di-Cl, 4-ClC6H4NH, yellow, 142° (decomposition); 3,4-di-Cl, 4-BrC6H4NH, pale brown, 141° (decomposition); 3,4-di-Cl, 2,3-Cl2C6H3NH, yellow, 154° (decomposition); 3,4-di-Cl, 2,5-di-Cl2C6H3NH, dark yellow, 146-7°; 3,4-di-Cl, 2,4-Cl2C6H3NH, yellow, 118-20° (decomposition); 3,4-di-Cl, 3,5-Cl2C6H3NH, (brown, 128-30°; 3,4-di-Cl, 3,4-Cl2C6H3NH, yellow, 151°; 3,4-di-Cl, 2,4,5-Cl3C6H2NH, yellow, 164° (decomposition); 2,6-di-Cl, 3,4-Cl2C6H3NH, -, 107-8°; 3,4-di-Cl, 4-(3,4-Cl2C6H3N:N)C6H4NH, yellow, 175-6° (decomposition). Similarly prepared was VII, yellow, m. 229-30° (decomposition) (EtOH). Also prepared were 2-methyl-4-(3,4-dichlorophenyl)-1,3,4-oxadiazol-5-one, m. 136-9° (EtOH), 3,4-Cl2C6H3NHCO(CH2)2Ac, m. 119-20° (EtOH), 4-ClC6H4CH2(NH)2COPh, m. 140-1° (EtOH), (4-ClC6H4CH2)2NNHCOPh, m. 180-2° (EtOH), (2-ClC6H4CH2)2NNHCOPh, m. 154-5° (EtOH), (3,4-Cl2C6H3CH2)2NNHCOPh, m. 145-6° (EtOH), (2-ClC6H4CH2)2NNHCH2C6H4Cl-p, m. 119-20° (EtOH), (2-ClC6H4CH2)2NNHAc, m. 128-9° (C6H6), and 3,4-Cl2C6H3CH2CH2(NH)2Ac, m. 140-1° (C6H6). Results of antibacterial and antifungal tests of all above compounds against Piricularia oryzae, Colletotrichum lagenarium, Xanthomonas oryzae, Fusarium oxysporum, Alternaria kikuchiana, Glomerella cingulata, Gibberella fujikuroi, Phytophthora infestans, Candida albicans, Trichophyton mentagrophytes, Corticium sasakii, Ophiobolus miyabeanus, Bacillus subtilis, Staphylococcus aureus, and Saccharomyces cerevisiae were also described.

Yakugaku Zasshi 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 C9H5ClO2, Product Details of C10H9ClN2O.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Usui, Yoshiro published the artcileFungicides. XII. Synthesis and antifungal activity of halogen-substituted phenylpyrazolone derivatives, HPLC of Formula: 14580-22-4, the publication is Yakugaku Zasshi (1967), 87(1), 38-42, database is CAplus and MEDLINE.

cf. CA 64: 14181e. A mixture of 1.5 g. I (X = 2,4,5-tri-Cl) and 0.9 g. Et acetoacetate is added to a mixture of 5 ml. AcOH and 5 ml. H2O, the whole heated 2 hrs., and 35 ml. H2O added to give 81% II, yellow needles, m. 58-60° (EtOH). I (0.02 mole) is heated in a mixture of 25 ml. AcOH and 10 ml. H2O with 0.02 mole Et acetoacetate for 2 hrs., the mixture evaporated in vacuo, the residue heated 5 hrs. with 25 ml. AcOH, evaporated in vacuo, and H2O added to the residue to give the following III (X, m.p., and % yield given): 2,3-di-Cl, 174-5°, 18; 2,6-di-Cl (red), 206°, 46; 2,4,5-tri-Cl (yellow), 199°, 81; 2,6-di-Br (yellow), 200-1°, 49. I (0.02 mole) and 0.02 mole Ac2O are added to 30 ml. C6H6, the whole boiled 3 hrs., cooled, and the precipitate recrystallized (C6H6) to give the following IV (X, m.p., and % yield given): 2-Cl, 118°, 62; 3-Cl, 131-2°, 62; 2,3-di-Cl, 136°, 73; 2,5-di-Cl, 159°, 97; 2,6-di-Cl, 153-5°, 93; 3,4-di-Cl, 168-71°, 77; 2,4,6-tri-Cl, 158°, 95.5; 2,6-di-Br, 158-61°, 58; 4-I, 159°, 74. PCl3 (1 mole) is dropped into a mixture of 1 mole each of IV and Et acetoacetate, the whole warmed 1.5 hrs. and poured into iced H2O, and the precipitate recrystallized from EtOH to give the following V (X, m.p., and % yield given): 2-Cl, 183-5°, 53; 3-Cl, 183°, 45; 4-Cl, 219-21°, 89; 2,3-di-Cl, 231-2°, 60; 2,6-di-Cl, 211-13°, 67; 3,4-di-Cl, yellow 208-9°, 76; 2,4,5-tri-Cl, yellow, 178-80°, 49; 2,4,6-tri-Cl, 193-4°, 49; 2,6-di-Br, 223-4°, 6.2; 4-I (brown), 214-16°, 37. Na (2.3 g.) is added to 40 ml. EtOH, boiled 17 hrs. with 6.2 g. Et cyanoacetate (VI) and 7.1 g. 4-chlorophenylhydrazine, and the mixture evaporated in vacuo. To the residue is added 120 ml. H2O, washed with Et2O, the residual aqueous solution neutralized with AcOH, and the solid recrystallized from MeOH to give 2.3 g. 1-(4-chlorophenyl)-3-aminopyrazolin-5-one, dark yellow needles, m. 169°. The use of Et cyclohexanone-2-carboxylate instead of VI in the above reaction gives 70% 2-(4-chlorophenyl)-4,5,6,7-tetrahydro-3-indazolinone, m. 186-7° (EtOH). Similarly prepared is 1-(4-chlorophenyl)-4,5,6,7-tetrahydro-3-indazolinone, m. 217-19° (EtOH). The relation between the structure of these compounds and their antifungal activity was examined using Corticium sasakii. It was found that antifungal activity tended to become weaker in the order phenylhydrazines > β-acetylphenylhydrazines > phenylhydrazones > phenylpyrazolones, and with the increasing number of halogens substituted.

Yakugaku Zasshi 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 C6H13I, HPLC of Formula: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Parekh, Nikhil published the artcileStudy on antibacterial activity for multidrug resistance stain by using phenyl pyrazolones substituted 3-amino 1H-pyrazolon (3,4-b) quinoline derivative in vitro condition, HPLC of Formula: 14580-22-4, the publication is International Journal of PharmTech Research (2011), 3(1), 540-548, database is CAplus.

3-Methyl-1-phenyl-4-[(E)-2-{1H-pyrazolo [3,4-b] quinolin-3-yl} diazen-1-yl]-4,5-dihydro-1H-pyrazol-5-one derivative have been synthesized by the reaction between substituted Ph pyrazolones and 3-amino-1 H-pyrazolo [3,4-b] quinoline. The novel compound structure has been established on the basis of their substituted Ph pyrazolones derivatives These compounds were tested for in vitro antifungal or antibacterial activity against Gram-Pos. and Gram-Neg. stain by standard method and synthesized compounds showed moderate to good antibacterial and antifungal activity with respect to standard drugs Ciprofloxacin and Flucanazole.

International Journal of PharmTech Research 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, HPLC of Formula: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Parekh, Nikhil published the artcileStudies on antimicrobial activity for multidrug resistance strain by using phenyl pyrazolones substituted 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one derivatives in vitro condition and their dyeing performance, SDS of cas: 14580-22-4, the publication is Fibers and Polymers (2012), 13(2), 162-168, database is CAplus.

Heterocyclic monoazo quinazolinone based azo dyes derived by the diazotization of 3-(4-aminophenyl)-2-phenylquinazolin-4(3H)-one with various Ph pyrazolones based coupling components. All the heterocyclic azo dyes were characterized by their percentage yield, UV-VIS spectroscopy, elemental anal., IR spectroscopy, ¹H NMR spectroscopy, and dyeing performance on silk, wool, nylon, and polyester fibers. All the dyes gave moderate to excellent fastness properties on each fiber. The main focus was to synthesize heterocyclic monoazo dyes that give good dyeing property along with pharmacol. activity (anti bacterial and antifungal). Therefore, the synthesized compounds were examined for their antimicrobial activity at various concentrations using well-known Kirby-Bauer disk diffusion method.

Fibers and Polymers 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, SDS of cas: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Chauhan, Pankaj published the artcileAsymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction, Category: pyrazoles-derivatives, the publication is Journal of Organic Chemistry (2017), 82(13), 7050-7058, database is CAplus and MEDLINE.

A new series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in asym. Mannich reactions with pyrazolones. The amino-bis-pyrazolone products are obtained in excellent yields and stereoselectivities by employing a very low loading of 1 mol % of a bifunctional squaramide organocatalyst. Depending on the substitution at position 4 of the pyrazolones, the new protocol allows for the generation of one or two tetrasubstituted stereocenters, including a one-pot version combing the Mannich reaction with a base-mediated halogenation.

Journal of Organic Chemistry 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, Category: pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Liang, Jie published the artcileHigh-selective one-pot synthesis of spirocyclopropane pyrazolones promoted by 4-dimethylaminopyridine, Recommanded Product: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Youji Huaxue (2019), 39(11), 3169-3175, database is CAplus.

A 4-dimethylaminopyridine (DMAP)-promoted high stereoselectivity method for the synthesis of polysubstituted spiropropane pyrazolone was developed. A series of target compounds were synthesized in high yields from pyrazolone, aromatic aldehydes and bromoacetate as raw materials and DMAP as a base via three-component one-pot reaction. This reaction has the advantages of simple operation, high yield and good diastereotopic selectivity. In addition, this synthetic method is of great value for the study of spiropropane.

Youji Huaxue 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, Recommanded Product: 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Xie, Chen published the artcileA facile catalytic Michael addition of pyrazolines to α,β-unsaturated carbonyl compounds, Related Products of pyrazoles-derivatives, the publication is Tetrahedron Letters (2012), 53(49), 6650-6653, database is CAplus.

A new highly efficient cascade reaction of pyrazolines with α,β-unsaturated carbonyl compounds catalyzed by DBU was reported. The process underwent the first deprotection/Michael addition reaction to give 4-substituted pyrazolines, e.g. I [R = Et, MeO, PhO, etc.; Ar = Ph, 4-ClC₆H₄], which were further converted into 4,4-di-substituted pyrazolones II via the second deprotection/Michael reaction. The mechanism for this reaction was also studied.

Tetrahedron Letters 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 C23H23ClN2O4, Related Products of pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wang, Yingjun published the artcileSynthesis of Neutral Brilliant Yellow 3GL, Computed Properties of 14580-22-4, the publication is Pige Huagong (2002), 19(4), 23-27, database is CAplus.

The neutral brilliant yellow 3GL was synthesized by condensing 2,4-diaminobenzenesulfonic acid with cyanuric chloride, condensing with aniline, diazotizing, and then coupling with 3- methyl-1-(2-chlorophenyl)-5(4H)-pyrazolone (I). The intermediate (I) was also synthesized from 2-chloroaniline by diazotization, reduction, hydrolysis, condensation with Et acetoacetate, and self-cyclization.

Pige Huagong 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 C4H5NS2, Computed Properties of 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

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