{"id":11849,"date":"2022-12-05T07:32:40","date_gmt":"2022-12-04T23:32:40","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11849"},"modified":"2022-12-05T07:32:40","modified_gmt":"2022-12-04T23:32:40","slug":"finar-i-l-s-team-published-research-in-journal-of-the-chemical-society-in-cas-13599-22-9-2","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11849","title":{"rendered":"Finar, I. L.’s team published research in Journal of the Chemical Society in | CAS: 13599-22-9"},"content":{"rendered":"

Finar, I. L. published the artcileReaction between aroylacetones and arylhydrazines<\/i><\/b>, Formula: C16H12N2O2<\/a>, the publication is Journal of the Chemical Society (1958), 200-4, database is CAplus.<\/p>\n

PhNHNH2<\/sub> and \u03bf-, m-, and p-nitrobenzoylacetones react to form only 5-\u03bf-, -m-, and -p-nitrophenyl-3-methyl-1-phenylpyrazoles (I), 3,1,-5-MePh(x-O2<\/sub>NC6<\/sub>H4<\/sub>)C3<\/sub>HN2<\/sub>, whereas BzCH2<\/sub>Ac and 2,4-(O2<\/sub>N)2<\/sub>C6<\/sub>H3<\/sub>NHNH2<\/sub> give both 1-(2,4-dinitrophenyl)-3-methyl-5-phenylpyrazole (II) and 1-(2,4-dinitrophenyl)-5-methyl-3-phenylpyrazole (III). The orientation of I (x = 3 or 4) (IIIa, IIIb) was established by reduction to the amine, diazotization, and treatment with H3<\/sub>PO2<\/sub> to give 3-methyl-1,5-diphenylpyrazole (IV). Similar treatment of I (x = 2) (IVa) gave 3-methyl-1-phenyl-1H-pyrazolo[4,5-c]cinnoline (V) instead of the expected methyldiphenylpyrazole. To prevent the formation of V, IVa was converted into the 4-Br derivative Reduction to the amine, followed by diazotization and treatment of the diazonium salt (VI) with H3<\/sub>PO2<\/sub> gave 4-bromo-3-methylpyrazolo[1,2-d]phenanthridine (VII). Oxidation of IV by boiling with KMnO4<\/sub> in dilute C5<\/sub>H5<\/sub>N gave authentic 1,5-diphenylpyrazole-3-carboxylic acid. PhNHNH2<\/sub> (1.3 g.) and 2.35 g. \u03bf-O2<\/sub>NC6<\/sub>H4<\/sub>COCH2<\/sub>Ac heated 10 min. in alc. at 35-40\u00b0 gave 3.17 g. yellow phenylhydrazone (IX), m. 156\u00b0 (cf. Koenigs and Freund, C.A. 42, 1935h). Heating 10 g. diketone in alc. with 5.4 g. PhNHNH2<\/sub> in alc. on a steam bath 5 min. gave 6.4 g. of another form of the phenylhydrazone (IXa), m. 136\u00b0, together with 7.5 g. IVa. Colorless IXa boiled in alc. and the solution cooled quickly gave IX. Both IX and IXa heated in alc. on a steam bath or recrystallized from CHCl3<\/sub>, AcOH, or C6<\/sub>H6<\/sub> slowly formed IVa. PhNHNH2<\/sub> (1.2 g.) and 2.3 g. m-O2<\/sub>NC6<\/sub>H4<\/sub>COCH2<\/sub>Ac refluxed 3 hrs. in alc. yielded 93% IIIa, m. 102-3\u00b0. Condensation of p-O2<\/sub>NC6<\/sub>H4<\/sub>COCl with AcCH2<\/sub>CO2<\/sub>Et in the presence of NaOMe in MeOH by an adaptation of the method of B\u00fclow and Hailer [Ber. 35, 932(1902)], dilution of the mixture with ice H2<\/sub>O, filtration, pouring the filtrate into cold AcOH, and extraction with Et2<\/sub>O yielded 48% p-O2<\/sub>NC6<\/sub>H4<\/sub>COCH2<\/sub>CO2<\/sub>Et, converted according to Knorr and J\u00f6dicke [Ber. 18, 2259(1885)] to 3-methyl-5-(p-nitrophenyl)-1-phenylpyrazole-4-carboxylic acid (X), m. 210\u00b0, and transformed by heating 3 hrs. at 240-50\u00b0 to IIIb, m. 111-12\u00b0, also obtained in 36% yield by refluxing 2.0 g. p-O2<\/sub>NC6<\/sub>H4<\/sub>COCH2<\/sub>Ac and 1.1 g. PhNHNH2<\/sub> in alc. BzCH2<\/sub>Ac (20 g.) in alc. and 16 g. 2,4-(O2<\/sub>N)2<\/sub>C6<\/sub>H3<\/sub>NHNH2<\/sub> in 32 ml. 98% H2<\/sub>SO4<\/sub> and 350 ml. hot alc. heated 10 min. on a steam bath and the mixture decanted gave 15.3 g. II, m. 137\u00b0 (alc. or AcOH). The decanted solution cooled and filtered yielded 2.1 g. III, m. 154\u00b0 (alc. or AcOH). IVa, II, and III in AcOH treated with excess Br at room temperature and filtered, the precipitate taken up in CHCl3<\/sub>, and the solution washed with aqueous Na2<\/sub>CO3<\/sub> and H2<\/sub>O gave 86, 93, and 91% of the corresponding 4-Br derivatives m. 141, 176, and 158\u00b0, resp. The nitro compounds IIIa, IIIb, and IVa (1 mole) in alc. heated 1 hr. on a steam bath with 8 moles SnCl2<\/sub> in concentrated HCl and the cooled solution made alk. with 30% NH4<\/sub>OH, the amine extracted with Et2<\/sub>O, and recrystallized (alc.) yielded the corresponding 5-aminophenyl-3-methyl-1-phenylpyrazoles (XI): m-amino (XIa), m. 161.5\u00b0; p-amino (XIb), m. 93\u00b0; \u03bf-amino (XIc), m. 96\u00b0, also obtained as a better product, m. 99\u00b0, by heating 17.5 g. IVa in 10 ml. 60% N2<\/sub>H4<\/sub>.H2<\/sub>O in alc. on a steam bath in the presence of 2 g. Pd-C. Similar reduction of 10 g. 4-Br derivative of IVa gave 5.1 g. 5-(\u03bf-aminophenyl)-4-bromo-3-methyl-1-phenylpyrazole (XId), m. 135\u00b0. X was converted by the procedure of K. and J. (loc. cit.) to the corresponding 5-(p-aminophenyl)-3-methyl-1-phenylpyrazole-4-carboxylic acid (XIe), m. 261\u00b0. II (8 g.) in 500 ml. alc. and 15 ml. 30% NH4<\/sub>OH saturated with H2<\/sub>S heated 1 hr. on a steam bath and evaporated, the crystalline product (5.3 g.) taken up in concentrated HCl and filtered, the filtrate diluted with H2<\/sub>O, and the precipitate crystallized gave 1-(4-amino-2-nitrophenyl)-3-methyl-5-phenylpyrazole (XII), m. 182\u00b0 (alc.). III (1.4 g.) in 60 ml. alc. and 3 ml. 30% NH4<\/sub>OH reduced with H2<\/sub>S yielded 54% 1-(4-amino-2-nitrophenyl)-5-methyl-3-phenylpyrazole, m. 170\u00b0 (alc. or ligroine). The aminophenylpyrazoles (0.6 g.) in 3 ml. concentrated HCl were diazotized 30 min. with 0.3 g. NaNO2<\/sub> in 0.5 ml. H2<\/sub>O and the solution poured into 7 ml. 30% H3<\/sub>PO2<\/sub>. XIa and XIb both gave IV, characterized as its Br derivative m. 75\u00b0. XIe gave authentic 3-methyl-1,5-diphenyl-pyrazole-4-carboxylic acid, m. 205\u00b0. The product obtained by heating 4-chloroquinaldine with excess PhNHNH2<\/sub> in a sealed tube at 200\u00b0 (K. and F., loc. cit.) was shown to be 3-(\u03bf-aminophenyl)-5-methyl-1-phenylpyrazole (XIII) since it gave 5-methyl-1,3-diphenylpyrazole (picrate, m. 108\u00b0). XIc gave V, m. 216\u00b0, also obtained when the diazonium salt solution was heated with alc. and Gattermann Cu powder or with boiling 50% H2<\/sub>SO4<\/sub>, or was made alk. with NaOH solution XId was similarly converted through the diazonium salt VI to VII, m. 140\u00b0. XII gave red needles, m. 108\u00b0, by the above procedure but deaminating by addition of 1 g. XII, in 12 ml. AcOH to 0.3 g. NaNO2<\/sub> in 1.5 ml. concentrated H2<\/sub>SO4<\/sub> at 5\u00b0, keeping the mixture 30 min. at 5\u00b0, heating 30 min. on a steam bath with 20 ml. alc., diluting with H2<\/sub>O, and extracting with Et2<\/sub>O gave authentic 3-methyl-1-(\u03bf-nitrophenyl)-5-phenylpyrazole, m. 104\u00b0. Reduction of the aminophenylpyrazoles with Na and alc. and evaporation, solution in concentrated H2<\/sub>SO4<\/sub>, and addition of aqueous NaNO2<\/sub> according to the Knorr pyrazoline reaction procedure gave red color with XIa, XIb, XIc, and 1-(\u03bf-aminophenyl)-3-methyl-5-phenylpyrazole (C.A. 51, 7357g), and a blue color with XIII.<\/p>\n

Journal of the Chemical Society 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, Formula: C16H12N2O2<\/a>.<\/p>\n

Referemce:
https:\/\/en.wikipedia.org\/wiki\/Pyrazole<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"

Journal of the Chemical Society 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, Formula: C16H12N2O2<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[819,131],"tags":[740],"class_list":["post-11849","post","type-post","status-publish","format-standard","hentry","category-13599-22-9","category-pyrazoles-derivatives","tag-m-w250-300"],"yoast_head":"\nFinar, I. L.'s team published research in Journal of the Chemical Society in | CAS: 13599-22-9 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Finar, I. 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