{"id":11768,"date":"2022-12-02T03:56:09","date_gmt":"2022-12-01T19:56:09","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=11768"},"modified":"2022-12-02T03:56:09","modified_gmt":"2022-12-01T19:56:09","slug":"arnold-z-s-team-published-research-in-collection-of-czechoslovak-chemical-communications-in-28-cas-19959-71-8","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=11768","title":{"rendered":"Arnold, Z.’s team published research in Collection of Czechoslovak Chemical Communications in 28 | CAS: 19959-71-8"},"content":{"rendered":"

Arnold, Z. published the artcileSynthetic reactions of dimethylformamide. XVI. Formylalion of \u03b3-picoline<\/i><\/b>, SDS of cas: 19959-71-8<\/a>, the publication is Collection of Czechoslovak Chemical Communications (1963), 863-8, database is CAplus.<\/p>\n

cf. CA 59, 439h. Treatment of \u03b3-picoline (I) with (Me2<\/sub>NCH:NMe2<\/sub>)+<\/sup>ClO4<\/sub>–<\/sup> (II) gave 4-(\u03b2-dimethylaminovinyl)pyridine (III) which reacted with IICONMe2<\/sub> (DMF) and COCl2<\/sub> to give \u03b1-(4-pyridyl)-\u03b2-dimethylaminoacrolein (IV), also obtained by treatment of I with DMF and COCl2<\/sub> or POCl3<\/sub>. Alk. hydrolysis of IV afforded 4-pyridylmalonic dialdehyde (V). V with N2<\/sub>H4<\/sub> gave 4-(4-pyridyl)pyrazole (VI), with H2<\/sub>NCONHNH2<\/sub> (VII), 4-(4-pyridyl)pyrazole-1-carboxamide (VIII), with H2<\/sub>NCSNHNH2<\/sub> (IX), \u03b1-(4-pyridyl)-\u03b2-thiosemicarbazinoacrolein (X), and with NH3<\/sub>, 5-(4-pyridyl)pyrimidine (XI). To a mixture obtained from 0.26 g. Na and 100 ml. liquid NH3<\/sub>, 1.86 g. I was added at -60\u00b0, followed, after 15 min., by 4 g. powd. II. After cooling and stirring for 15 addnl. min., the NH3<\/sub> was evaporated, the residue treated with 20 ml. C6<\/sub>H6<\/sub> and 3 ml. H2<\/sub>O, the aqueous layer extracted with C6<\/sub>H6<\/sub>, the extract washed with H2<\/sub>O, dried, filtered, and evaporated to give 1.55 g. (52%) III, m. 101-2\u00b0 (MeCOEt at -60\u00b0). Adding 1.5 g. III to a solution prepared by adding 5 ml. 3N COCl2<\/sub> in CHCl3<\/sub> to 3.65 g. DMF in 25 ml. CHCl3<\/sub>, stirring the mixture 30 min. at room temperature, refluxing 6 hrs., treating with a saturated solution of K2<\/sub>CO3<\/sub>, extracting with 1:1 C6<\/sub>H6<\/sub>-EtOH, evaporating, and extracting the residue with C6<\/sub>H6<\/sub> gave 1.4 g. (79%) IV, Rf<\/sub> 0.65 (Whatman Number 4 paper in MeCOEt-H2<\/sub>O), m. 90-2\u00b0 (MeCOEt at -70\u00b0), also obtained by adding 1.86 g. I to a reagent prepared from 21.9 g. DMF and 9.2 g. POCl3<\/sub>, heating the mixture 6 hrs. at 70\u00b0, adding it to 70 ml. saturated solution of K2<\/sub>CO3<\/sub> covered with 30 ml. 1:1 C6<\/sub>H6<\/sub>EtOH, filtering the salts, extracting the filtrate with the above mixture, drying the extract with anhydrous K2<\/sub>CO3<\/sub>, evaporating, extracting the residue with C6<\/sub>H6<\/sub>, and evaporating to dryness in vacuo, yield 3.2 g. (91%) crude, 2.4 g. (68%) pure. IV was also obtained in 51% yield by stirring a mixture of 0.93 g. I in 3 ml. CHCl3<\/sub>, 7.3 g. DMF in 25 ml. CHCl3<\/sub>, and 10 ml. 3N COCl2<\/sub> in CHCl3<\/sub> 1 hr. at room temperature and 5 hrs. at reflux. Heating 0.176 g. IV with 0.11 g. 50% KOH and a few drops H2<\/sub>O to 70\u00b0, cooling the mixture, precipitating with concentrated KOH a potassium salt of V, filtering it off with suction, dissolving in H2<\/sub>O, and acidifying the solution gave V, m. >320\u00b0 (H2<\/sub>O), also obtained in 80% yield by heating a mixture of 21.9 g. DMF, 9.2 g. POCl3<\/sub>, and 1.86 g. I 6 hrs. at 70\u00b0, cooling, treating with 70 g. ice and a solution of 12 g. NaOH in 20 ml. H2<\/sub>O at 20\u00b0, heating the mixture 10 min. at 90\u00b0, cooling, and acidifying with 1:1 HCl to pH 7. Treatment of 0.15 g. V with an equal amount of 90% N2<\/sub>H4<\/sub> afforded VI, m. 198-9\u00b0 (H2<\/sub>O). Mixing a solution of 0.15 g. V in 6 ml. N HCl with a solution of 0.11 g. VII.HCl in 3 ml. N HCl gave VIII, m. 230\u00b0. Similar treatment of V with 0.09 g. IX gave X, m. 200\u00b0. Heating 0.3 g. V with 10 ml. NH3<\/sub> in EtOH 3 hrs. at 120\u00b0 in a stainless steel autoclave, filtering the mixture with activated C, and evaporating in vacuo gave 0.12 g. XI, m. 107.5-8.5\u00b0 (MeCOEt).<\/p>\n

Collection of Czechoslovak Chemical Communications published new progress about 19959-71-8. 19959-71-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Pyridine, name is 4-(1H-Pyrazol-4-yl)pyridine, and the molecular formula is C8H7N3, SDS of cas: 19959-71-8<\/a>.<\/p>\n

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

Collection of Czechoslovak Chemical Communications published new progress about 19959-71-8. 19959-71-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Pyridine, name is 4-(1H-Pyrazol-4-yl)pyridine, and the molecular formula is C8H7N3, SDS of cas: 19959-71-8<\/a>.<\/p>\n","protected":false},"author":8,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[803,131],"tags":[732],"class_list":["post-11768","post","type-post","status-publish","format-standard","hentry","category-19959-71-8","category-pyrazoles-derivatives","tag-m-w100-150"],"yoast_head":"\nArnold, Z.'s team published research in Collection of Czechoslovak Chemical Communications in 28 | CAS: 19959-71-8 | pyrazoles-derivatives<\/title>\n<meta name=\"description\" content=\"Arnold, Z. published the artcileSynthetic reactions of dimethylformamide. XVI. 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