CS235196B1 - 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 PDFInfo
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- CS235196B1 CS235196B1 CS841307A CS130784A CS235196B1 CS 235196 B1 CS235196 B1 CS 235196B1 CS 841307 A CS841307 A CS 841307A CS 130784 A CS130784 A CS 130784A CS 235196 B1 CS235196 B1 CS 235196B1
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Abstract
Vynález se týká nového způsobu přípravy 4,9-dihydro-3,9-dimethyl-4-oxo-lH-pyrazolo- (3,4-bjohinolinu, vyznačujícího se tím, že se zahřívá 4,9-dihydro-2,3,9-trimethyl-4-oxo-2H- -pyrazolo[ 3,4-b ] chinolin s hydrochloridem pyridinu na teplotu 200 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-2,3,9-trimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline is heated with pyridine hydrochloride to a temperature of 200 to 240 °C, preferably to a temperature of 220 °C.
Description
Vynález se týká nového způsobu přípravyThe invention relates to a novel preparation process
4,9-dihydro-3,9-dimethyl-4-oxo-lH-pyrazolo[3,4-b]chinolinu vzorce I4,9-Dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo [3,4-b] quinoline of Formula I
Uvedená sloučenina vzorce I slouží jako meziprodukt pro přípravu biologicky významných látek, zejména s protivirovým účinkem.Said compound of formula (I) serves as an intermediate for the preparation of biologically important substances, in particular having antiviral activity.
Uvedená sloučenina vzorce I je známá látka, je popsána její příprava, vyznačující se tím, že se zahřívá 4-(2-fluorfenyl-6,3-dihydro-l,3,8-trimethylpyrazolo (3,4-e )(1,4) diazepin-7(lH)on s hydrochloridem pyridinu na teplotu 210 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-6,3-dihydro-1,3,8-trimethylpyrazolo (3,4-e) (1, 2-fluorophenyl)). 4) diazepin-7 (1H) on with pyridine hydrochloride at 210-215 ° 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-2,3,9-trimethyl-4-oxo-2H-pyrazolo (3,4-b) chinolin (čs. autorské osvědčení č. 235 168 s hydrochloridem pyridinu při teplotě 200 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-2,3,9-trimethyl-4-oxo-2H-pyrazolo (3,4-b) quinoline (U.S. Pat. No. 235 168 with pyridine hydrochloride at a temperature of 200 to 240 ° C, preferably at a temperature of 220 ° C.
Vzhledem ke snadné připravitelnosti výchozího 4,9-dlhydro-2,3,9-trimethyl-4-oxo-2H-pyrazolof 3,4-b) chinolinu (čs. autorské osvědčení čís. 235168), a vzhledem k obtížné přípravě 4- (2-fluorfenyl)6,8-dihydro-l,3,8-trimethylpyrazolo[ 3,4-e] ((l,4]diazepin-7(lH)onu, je zřejmá výhodnost přípravy sloučeniny vzorce I podle vynálezu.Given the ease of preparation of the starting 4,9-dlhydro-2,3,9-trimethyl-4-oxo-2H-pyrazolof 3,4-b) quinoline (cf. No. 235168), and the difficult preparation of 4- (2-fluorophenyl) 6,8-dihydro-1,3,8-trimethylpyrazolo [3,4-e] ((1,4) diazepin-7 (1H) -one), the advantageous preparation of the compound of formula I of the invention is evident.
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 ] chinolin > Z míchané směsi 30 g pyridinu a 44 ml koncentrované kyseliny chlorovodíkové byla postupným zvyšováním teploty na 160 °C oddestilována voda. Při této teplotě bylo přidáno 3,2 g 4,9-dihydro-2,3,9-trimethyl-4-oxo-2H-pyrazolo[ 3,4-b] chinolin 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 odfiltrován. Látka vyloučená po ochlazení filtrátu byla odsáta a promyta vodou. Krystaly získané krystalizací z ethanolu byly sušeny do konstantní hmotnosti při teplotě 110 °C za tlaku 3 kPa. Bylo získáno 2,32 g látky (77,7 %) o t. t. 248,8 až 249,5 °C.4,9-Dihydro-3,9-dimethyl-4-oxo-1H-pyrazolo [3,4-b] quinoline Water was distilled from a stirred mixture of 30 g of pyridine and 44 ml of concentrated hydrochloric acid by gradually increasing the temperature to 160 ° C. . At this temperature, 3.2 g of 4,9-dihydro-2,3,9-trimethyl-4-oxo-2H-pyrazolo [3,4-b] quinoline was added and the mixture was stirred at 220 ° C for 2 hours. After cooling to 160 ° C, the mixture was poured into 240 ml of water, the mixture was boiled and the insoluble matter was filtered off. The precipitate upon cooling of the filtrate was aspirated and washed with water. Crystals obtained by crystallization from ethanol were dried to constant weight at 110 ° C at 3 kPa. 2.32 g (77.7%) of m.p. 248.8-249.5 ° C were obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Applications Claiming Priority (2)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235196B1 true CS235196B1 (en) | 1985-05-15 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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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| CS (2) | CS235197B1 (en) |
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1984
- 1984-02-24 CS CS841308A patent/CS235197B1/en unknown
- 1984-02-24 CS CS841307A patent/CS235196B1/en unknown
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| CS235197B1 (en) | 1985-05-15 |
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