CS235183B1 - Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline - Google Patents

Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline Download PDF

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CS235183B1
CS235183B1 CS838460A CS846083A CS235183B1 CS 235183 B1 CS235183 B1 CS 235183B1 CS 838460 A CS838460 A CS 838460A CS 846083 A CS846083 A CS 846083A CS 235183 B1 CS235183 B1 CS 235183B1
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Czechoslovakia
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dihydro
pyrazolo
oxo
quinoline
preparation
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CS838460A
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Czech (cs)
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Viktor Zikan
Stanislav Radl
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Viktor Zikan
Stanislav Radl
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Priority to CS838460A priority Critical patent/CS235183B1/en
Priority to CS841307A priority patent/CS235196B1/en
Priority to CS841308A priority patent/CS235197B1/en
Publication of CS235183B1 publication Critical patent/CS235183B1/en

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Abstract

Vynález se týká nového způsobu přípravy 4,9-dihydro-3,9-dimethyl-4-oxo-lH-pyrazolo- (3,4-b)chinolinu, vyznačujícího se tím, že se zahřívá 4,9-dihydro-l,3,9-trimethyl-4-oxo-lH- -pyrazolo'(3,4-b)cihinolin s hydrochloridem pyridinu na teplotu 200 °C až 240 °C, výhodně na teplotu 220 °C.The invention relates to a new process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo-(3,4-b)quinoline, characterized in that 4,9-dihydro-1,3,9-trimethyl-4-oxo-1H-pyrazolo'(3,4-b)quinoline is heated with pyridine hydrochloride to a temperature of 200 °C to 240 °C, preferably to a temperature of 220 °C.

Description

Uvedená sloučenina vzorce I slouží jako meziprodukt pro přípravu biologicky významných látek, zejména s protivirovým účinkem podle čs. autorského osvědčení č. 235 168.Said compound of formula (I) serves as an intermediate for the preparation of biologically important substances, in particular with antiviral activity according to U.S. Pat. Certificate No. 235 168.

Uvedená sloučenina vzorce I je známá látka, je popsána její příprava, vyznačující se tím, že se zahřívá 4-(2-f luorfenyl)-6,8-dihydro-l,3,8-trimethylpyrazolo( 3,4-e) (1,4) diazepin-7(lH]on s hydrochloridem pyridinu na teplotu 210 °C až 215 °C (DeWald H. A.: J. Heterocyclic Chem. 11, 1061 (1974)].Said compound of formula (I) is a known substance, the preparation of which is characterized by heating 4- (2-fluorophenyl) -6,8-dihydro-1,3,8-trimethylpyrazolo (3,4-e) ( 1,4) diazepin-7 (1H) on with pyridine hydrochloride at 210 ° C to 215 ° C (DeWald HA: J. Heterocyclic Chem. 11, 1061 (1974)).

Uvedená sloučenina vzorce I byla připravena způsobem podle vynálezu, vyznačující se tím, že se zahřívá 4,9-dihydro-l,3,9-trimethyl-4-oxo-lH-pyrazolo (3,4-b) chinolin (čs. autorské osvědčení č. 235 167], s hydrochloridem pyridinu při teplotě 200 °C až 240 °C, výhodně při teplotě 220 °C.Said compound of formula (I) was prepared by the process of the invention, characterized by heating 4,9-dihydro-1,3,9-trimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline (U.S. Pat. No. 235 167], with pyridine hydrochloride at a temperature of 200 ° C to 240 ° C, preferably at a temperature of 220 ° C.

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Claims (4)

Způsob přípravy 4,9-dihydro-3,9-dimethyl-4-oxo-lH-pyrazolo (3,4-b j chino linu, vyznačující se tím, že se zahřívá 4,9-dihydro-l,3,9Vzhledem ke snadné připravitelnosti výchozího 4,9-dihydro-l,3,9-trimethyl-4-oxo-lH-pyrazolo( 3,4-b jchinolinu (čs. autorské osvědčení č. 235 167 a vzhledem k obtížné přípravě 4- (A process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo [3,4-b] quinoline characterized in that 4,9-dihydro-1,3,9 is heated. the preparability of the starting 4,9-dihydro-1,3,9-trimethyl-4-oxo-1H-pyrazolo [3,4-b] quinoline (U.S. Pat. No. 235,167) and due to the difficult preparation of 4- ( 2-f luorfenyl) -6,8-dihydr o-l,2-fluorophenyl) -6,8-dihydrol-1, 3,8-trimethylpyrazolo (3,4-e )(1,4) diazepin-7 (1H) onu je zřejmá výhodnost přípravy sloučeniny vzorce podle vynálezu.3,8-trimethylpyrazolo (3,4-e) (1,4) diazepin-7 (1H) -one is a clear advantage of the preparation of a compound of the invention. Následující příklad provedení vynález dokládá, ale nikterak neomezuje.The following exemplary embodiment illustrates the invention but does not limit it in any way. PříkladExample 4,9-Dihydro-3,9-dimethyl-4-oxo-lH-pyrazolo( 3,4-b) chinolin4,9-Dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline Z míchané směsi 30 g pyridinu a 44 ml koncentrované kyseliny chlorovodíkové byla postupným zvyšováním teploty na 160 °C odlestilována voda. Při této teplotě bylo přidáno 3,2 g 4,9-dihydro-l,3,9-trimethyl-4-oxo-lH-pyrazolo(3,4-b jchinolinu a směs byla míchána 2 hodiny při teplotě 220 °C. Po ochlazení na 160 °C byla směs nalita do 240 ml vody, směs byla povařena a nerozpustný podíl byl filtrován. Látka vyloučená po ochlazení filtrátu byla odsáta a promyta vodou. Krystaly získané krystalizaci z ethanolu byly sušeny do konstantní hmotnosti při teplotě 110 °C za tlaku 3 kPa. Bylo získáno 2,35 g látky (78,7%) o t. t. 248,7 °C až 249,5 °C.Water was distilled from the stirred mixture of pyridine (30 g) and concentrated hydrochloric acid (44 ml) by gradually increasing the temperature to 160 ° C. At this temperature, 3.2 g of 4,9-dihydro-1,3,9-trimethyl-4-oxo-1H-pyrazolo (3,4-bquinoline) was added and the mixture was stirred at 220 ° C for 2 hours. After cooling to 160 DEG C., the mixture was poured into 240 ml of water, the mixture was boiled and the insoluble matter was filtered. 2.35 g (78.7%) of mp 248.7 ° C to 249.5 ° C were obtained. VYNALEZUVYNALEZU -trimethyl-4-oxo-lH-pyrazolo( 3,4-b) chinolin s hydrochloridem pyridinu při teplotě 200 °C až 240 °C, výhodně při teplotě 220 °C.- trimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline with pyridine hydrochloride at a temperature of 200 ° C to 240 ° C, preferably at 220 ° C.
CS838460A 1983-09-09 1983-11-15 Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline CS235183B1 (en)

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Application Number Priority Date Filing Date Title
CS838460A CS235183B1 (en) 1983-09-09 1983-11-15 Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline
CS841307A CS235196B1 (en) 1983-11-15 1984-02-24 Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline
CS841308A CS235197B1 (en) 1983-11-15 1984-02-24 Process for preparing 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinolines

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CS658683A CS235167B1 (en) 1983-09-09 1983-09-09 Substituted 4,9-dihydro-3-methyl-4-oxo-1H-pyrazole (3,4-b quinolines and process for their preparation)
CS838460A CS235183B1 (en) 1983-09-09 1983-11-15 Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline

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CS658683A CS235167B1 (en) 1983-09-09 1983-09-09 Substituted 4,9-dihydro-3-methyl-4-oxo-1H-pyrazole (3,4-b quinolines and process for their preparation)
CS838460A CS235183B1 (en) 1983-09-09 1983-11-15 Process for the preparation of 4,9-dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline
CS838459A CS235182B1 (en) 1983-09-09 1983-11-15 Preparation of 4,9-dihydro-1,3-dinityl-4-oxo-1H-pyrazolo (3,4-b) -quinoline
CS839743A CS235188B1 (en) 1983-09-09 1983-12-21 4,9-Dihydro-1- (2,3-dihydroxypropyl) -3-methyl-4-oxo-1H-pyrazolo- (3,4-b) quinoline and its method of preparation
CS841309A CS235198B1 (en) 1983-09-09 1984-02-24 4- (1-Alkyl-2-hydroxyethylamino) -3-methyl-1 - [(2,2-dimethyl-1,3-dioxolan-4-yl) methyl] -1H-pyrazolo (3,4-bquinolines and the method of their preparation
CS841310A CS235199B1 (en) 1983-09-09 1984-02-24 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation

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CS838459A CS235182B1 (en) 1983-09-09 1983-11-15 Preparation of 4,9-dihydro-1,3-dinityl-4-oxo-1H-pyrazolo (3,4-b) -quinoline
CS839743A CS235188B1 (en) 1983-09-09 1983-12-21 4,9-Dihydro-1- (2,3-dihydroxypropyl) -3-methyl-4-oxo-1H-pyrazolo- (3,4-b) quinoline and its method of preparation
CS841309A CS235198B1 (en) 1983-09-09 1984-02-24 4- (1-Alkyl-2-hydroxyethylamino) -3-methyl-1 - [(2,2-dimethyl-1,3-dioxolan-4-yl) methyl] -1H-pyrazolo (3,4-bquinolines and the method of their preparation
CS841310A CS235199B1 (en) 1983-09-09 1984-02-24 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation

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CS235188B1 (en) 1985-05-15
CS235167B1 (en) 1985-05-15
CS235199B1 (en) 1985-05-15
CS235182B1 (en) 1985-05-15

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