PL147339B2 - Method for producing a new passive component for manufacturing azo dyes - Google Patents

Method for producing a new passive component for manufacturing azo dyes Download PDF

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Publication number
PL147339B2
PL147339B2 PL26195886A PL26195886A PL147339B2 PL 147339 B2 PL147339 B2 PL 147339B2 PL 26195886 A PL26195886 A PL 26195886A PL 26195886 A PL26195886 A PL 26195886A PL 147339 B2 PL147339 B2 PL 147339B2
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passive component
azo dyes
producing
new passive
formula
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PL26195886A
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Polish (pl)
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PL261958A2 (en
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Przedmiotem wynalazku jest sposób otrzymywania nowego skladnika biernego do wytwarza¬ nia barwników azowych, kwasu 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimidynokarboksylowego o wzorze 1.Sposobem wedlug wynalazku 2-perimidynylooctan etylu o wzorze 2 poddaje sie reakcji z diketenem w pirydynie, po czym na uzyskany l-acetoacetonyloperimidyn-2-ylooctan etylu dziala sie etanolanem sodu w pirydynie. Uzyskany w toku syntezy jako zwiazek przejsciowy 1- acetoacetonyloperimidyn-2-ylooctan etylu jest równiez nowym zwiazkiem.Wynalazek ilustruje nastepujacy przyklad, w którym procenty oznaczaja procenty wagowe, a stopnie temperatury podano w stopniach Celsjusza.Przyklad . W kolbie okraglodennej o pojemnosci 250cm3, zaopatrzonej w chlodnice zwrotna, umieszczono 2,54 g (0,01 mola) 2-perimidynylooctanu etylu, 10 cm3 bezwodnej pirydyny i dodano stopniowo, przy intensywnym mieszaniu, 1 g (okolo 0,012 mola) deketenu. Egzotermiczna reakcja zachodzi natychmiastowo, po krótkim czasie wypada krystalicznyprodukt. Po godzinnym ogrzewaniu i mieszaniu w temperaturze 80 — 90° dodano 100 cm3 wody i po dokladnym wymiesza¬ niu odsaczono surowy produkt. Otrzymano 3,20 g l-acetoacetonyloperimidyn-2-ylooctanu etylu o temperaturze topnienia 158 — 165°. Wydajnosc wyniosla 96%. Surowy produkt oczyszczono przez krystalizacje z etanolu, uzyskujac zwiazek koloru zóltego o postaci igiel o temperaturze topnienia 159_164°.Analiza dla wzoru C19H18N2O4: obliczono C 67,4, H 5,4 i N 8,3% otrzymano C 67,4, H 5,4 i N 8,2% IR (KBr) cm"1:1720 (C = 0), 1630 i 1620 (C = C,C = N), 1580,1380,1285,1170ii 100 (C —0), 705.W kolbie okraglodennej o pojemnosci 250 cm3 z chlodnica zwrotna zabezpieczona przed wilgocia umieszczono 3,38 g (0,01 mola) otrzymanego opisanym wyzej sposobem 1-acetoaceto- nyloperimidyn-2-ylooctanu etylu w 20 cm3 bezwodnej pirydyny, a nastepnie dodano stopniowo, przy intensywnym mieszaniu, roztwór etanolanu sodowego uzyskany w reakcji 0,5 g sodu w 20 cm32 147 339 etanolu. Mieszanine reakcyjna ogrzewano przez 1 godzine w temperaturze 80 — 90° przy intensyw¬ nym mieszaniu, po czym dodano 80 cm wody i zobojetniono kwasem octowym. Krystaliczny produkt odasaczono, przemyto woda i osuszono. Uzyskano 2,54 g zóltego produktu o temperatu¬ rze topnienia 275 — 279° (z rozkladem). Wydajnosc wyniosla 86%. Produkt analitycznie czysty uzyskano po krystalizacji z dimetyloformamidu.Analiza dla wzoru C17H12N2O3: obliczono C 69,9, H 4,2 i N 9,6% otrzymano C 69,7, H4,2 i N 9,6% IR (KBr) cm"1: 1680 (C = 0), 1630 (C = C, C =N), 1580, 1410, 990, 705 1H — NMR (CF3COOH), 6 (ppm): 7,0 — 7,35 (m, 4H, CH arom., C — 6,7,8,9); 6,4 — 6,5 (m, 2H, CHarom., C — 5,10); 6,3 (s, 1H, CH — 3); 2,3 (s, 3H, CH3-).Zastrzezenie patentowe Sposób otrzymywania nowego skladnika biernego do wytwarzania barwników azowych, kwasu 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimidynokarboksylowego o wzorze 1, znamienny tym, ze 2-perimidynylooctan etylu o wzorze 2 poddaje sie reakcji z diketenem w pirydynie, po czym na uzyskany l-acetoacetonyloperimidyn-2-ylooctan etylu dziala sie etanolanem sodu w pirydynie. 0 CH3 H,CX WZÓR 1 0 CHjD0CH2CH3 N^NH WZtfR 2 CHaC0CH2CH3 WZ0R 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 400 zl PLThe subject of the invention is a process for the preparation of a new passive component for the production of azo dyes, 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidinecarboxylic acid of the formula 1. The method of the invention is After the reaction with diketene in pyridine, the resulting ethyl 1-acetoacetonyl perimidin-2-ylacetate is treated with sodium ethoxide in pyridine. Ethyl 1-acetoacetonyl perimidin-2-ylacetate, obtained in the course of synthesis as an intermediate compound, is also a new compound. The invention is illustrated by the following example, in which the percentages are percentages by weight and the degrees of temperature are given in degrees Celsius. In a 250 cm3 round bottom flask equipped with reflux condensers, 2.54 g (0.01 mol) of ethyl 2-perimidinylacetate, 10 cm3 of anhydrous pyridine were added and 1 g (about 0.012 mol) of decetene was gradually added with intense stirring. The exothermic reaction takes place immediately and a crystalline product falls out after a short time. After heating for 1 hour and stirring at 80-90 °, 100 cm 3 of water are added and, after stirring thoroughly, the crude product is filtered off. 3.20 g of ethyl 1-acetoacetonyl perimidin-2-ylacetate were obtained, mp 158-165 °. The yield was 96%. The crude product was purified by crystallization from ethanol to give a yellow needle compound, m.p. 159-164 °. Analysis for formula C19H18N2O4: calculated C 67.4, H 5.4 and N 8.3%. C 67.4, H 5 , 4 and N 8.2% IR (KBr) cm -1: 1720 (C = 0), 1630 and 1620 (C = C, C = N), 1580,1380,1285,1170ii 100 (C -0), 705. In a 250 cm3 round bottom flask with a reflux condenser protected against moisture, 3.38 g (0.01 mol) of ethyl 1-acetoacetonyl perimidin-2-ylacetate, prepared as described above, were placed in 20 cm3 of anhydrous pyridine, and then added gradually. with vigorous stirring, a solution of sodium ethoxide obtained in the reaction of 0.5 g of sodium in 20 cm3 of ethanol. The reaction mixture was heated for 1 hour at the temperature of 80-90 ° under intense stirring, then 80 cm of water was added and neutralized with acid. The crystalline product was deselected, washed with water and dried to give 2.54 g of a yellow product, mp 275-279 ° (from zkladem). The yield was 86%. Analytically pure product was obtained after crystallization from dimethylformamide. Analysis for the formula C17H12N2O3: calculated C 69.9, H 4.2 and N 9.6% obtained C 69.7, H4.2 and N 9.6% IR (KBr) cm "1: 1680 (C = 0), 1630 (C = C, C = N), 1580, 1410, 990, 705 1H - NMR (CF3COOH), 6 (ppm): 7.0 - 7.35 (m, 4H, CH arom, C - 6.7, 8.9); 6.4 - 6.5 (m, 2H, CHarom, C - 5.10); 6.3 (s, 1H, CH - 3 ); 2,3 (s, 3H, CH3 -). Claim A method of obtaining a new passive component for the production of azo dyes, 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidine carboxylic acid of formula 1, characterized in that ethyl 2-perimidinylacetate of formula 2 is reacted with diketene in pyridine and the resulting ethyl 1-acetoacetonylperimidin-2-ylacetate is treated with sodium ethoxide in pyridine. 0 CH3H, CX FORMULA 1 0 CHiD0CH2CH3 N4NH WZtfR 2 CHaC0CH2CH3 WZ0R 3 Printing House of the Polish People's Republic of Poland. Circulation 100 copies Price PLN 400 PL

Claims (2)

Zastrzezenie patentowe 1. Sposób otrzymywania nowego skladnika biernego do wytwarzania barwników azowych, kwasu 4-hydroksy-2-metylo-l-pirydo[l,2-a]perimidynokarboksylowego o wzorze 1, znamienny tym, zeClaim 1. A method for the preparation of a new passive component for the production of azo dyes, 4-hydroxy-2-methyl-1-pyrido [1,2-a] perimidinecarboxylic acid of formula 1, characterized by 2. -perimidynylooctan etylu o wzorze 2 poddaje sie reakcji z diketenem w pirydynie, po czym na uzyskany l-acetoacetonyloperimidyn-2-ylooctan etylu dziala sie etanolanem sodu w pirydynie. 0 CH3 H,CX WZÓR 1 0 CHjD0CH2CH3 N^NH WZtfR 2 CHaC0CH2CH3 WZ0R 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 400 zl PLEthyl 2-perimidinylacetate of the formula II is reacted with diketene in pyridine and the resulting ethyl 1-acetoacetonylperimidin-2-ylacetate is treated with sodium ethoxide in pyridine. 0 CH3 H, CX MODEL 1 0 CHjD0CH2CH3 N ^ NH WZtfR 2 CHaC0CH2CH3 WZ0R 3 Printing workshop of the PRL. Mintage 100 copies. Price PLN 400 PL
PL26195886A 1986-10-20 1986-10-20 Method for producing a new passive component for manufacturing azo dyes PL147339B2 (en)

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PL26195886A PL147339B2 (en) 1986-10-20 1986-10-20 Method for producing a new passive component for manufacturing azo dyes

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PL26195886A PL147339B2 (en) 1986-10-20 1986-10-20 Method for producing a new passive component for manufacturing azo dyes

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PL147339B2 true PL147339B2 (en) 1989-05-31

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