CS235182B1 - Preparation of 4,9-dihydro-1,3-dinityl-4-oxo-1H-pyrazolo (3,4-b) -quinoline - Google Patents
Preparation of 4,9-dihydro-1,3-dinityl-4-oxo-1H-pyrazolo (3,4-b) -quinoline Download PDFInfo
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- CS235182B1 CS235182B1 CS838459A CS845983A CS235182B1 CS 235182 B1 CS235182 B1 CS 235182B1 CS 838459 A CS838459 A CS 838459A CS 845983 A CS845983 A CS 845983A CS 235182 B1 CS235182 B1 CS 235182B1
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- quinoline
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Abstract
Vynález se týká nového způsobu přípravy 4,9-dihydro-l,3-dimethyl-4-oxo-lH-pyrazolo- (3,4-b Jchinolinu, vyznačujícího se tím, že se hydrolyzuje 4-cihlor-l,3-dimethyl-lH-pyrazolo( 3,4-b Jchiholin varem s kyselinou chlorovodíkovou.The invention relates to a new process for the preparation of 4,9-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo-(3,4-b)quinoline, characterized in that 4-dichloro-1,3-dimethyl-1H-pyrazolo-(3,4-b)quinoline is hydrolyzed by boiling with hydrochloric acid.
Description
(54) Způsob přípravy 4,9-dihydro-l,3-dinwthyl-4-oxo-lH-pyrazolo(3,4-b)chinolinu(54) A method for preparing 4,9-dihydro-1,3-dinyl-4-oxo-1H-pyrazolo (3,4-b) quinoline
Vynález se týká nového způsobu přípravyThe invention relates to a novel preparation process
4,9-dihydro-l,3-dimethyl-4-oxo-lH-pyrazolo(3,4-bjchinolinu, vyznačujícího se tím, že se hydrolyzuje 4-cihlor-l,3-dimethyl-lH-pyrazolo(3,4-b)chiholin varem s kyselinou chlorovodíkovou.4,9-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo [3,4-b] quinoline characterized by the hydrolysis of 4-brick-1,3-dimethyl-1H-pyrazolo (3,4-quinoline) (b) chiholine by boiling with hydrochloric acid.
Vynález se týká nového způsobu přípravyThe invention relates to a novel preparation process
4,9-dihydro-l,3-dimethyl-4-oxo-lH-pyrazolo(3,4-b) chinolínu vzorce I4,9-Dihydro-1,3-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 podle čs. autorského osvědčení číslo 235 167.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. 235 167.
Uvedená sloučenia vzorce I je známá látka, je popsána její příprava z N-(l,3-dimethyl-5-pyrazolyl)anthranilové kyseliny [Stein R. G., Biel J. H.: Med. Chem. 13, 153 (1973)], nebo z 5-amino-4-(2-fluorbenzoyl)-l,3-dimetylpyrazolu [DeWald H. A.: j. Heterocyclic Chem. 11, 1061 (1974)].Said compound of formula I is a known compound, its preparation from N- (1,3-dimethyl-5-pyrazolyl) anthranilic acid [Stein R. G., Biel J. H .: Med. Chem. 13, 153 (1973)], or from 5-amino-4- (2-fluorobenzoyl) -1,3-dimethylpyrazole [DeWald H. A., J. Heterocyclic Chem. 11, 1061 (1974)].
182182
Uvedená sloučenina vzorce I byla připravena způsobem podle vynálezu, vyznačující se tím, že se obecně známý 4-chlor-l,3-dimethyl-lH-pyrazolo(3,4-b)chinolin [Stein R. G., Biel J. H.: J. Med. Chem. 13, 153 (1973)] hydrolyzuje varem s O,1M až 5M roztokem kyseliny chlorovodíkové, s výhodou s IM kyselinou chlorovodíkovou.Said compound of formula (I) was prepared by the process of the invention, characterized in that the generally known 4-chloro-1,3-dimethyl-1H-pyrazolo (3,4-b) quinoline [Stein, R.G., Biel, J. H .: J. Med. Chem. 13, 153 (1973)] hydrolyzes by boiling with a 0.1M to 5M hydrochloric acid solution, preferably 1M hydrochloric acid.
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-l,3-dimethyl-4-oxo-lH-pyrazolo(3,4-b)chinolin4,9-Dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline
Směs 2,32 g 4-chlor-l,3-dimethyl-lH-pyrazolo(3,4-b)chinolinu (10 mmol) a 23 ml IM kyseliny chlorovodíkové byla 2 hodiny vařena pod zpětným chladičem. Po ochlazení reakční směsi byl přidán vodný amoniak do dosažení pH 8 a poté byla směs zneutralizována kyselinou octovou. Nerozpustný podíl byl odsát, promyt vodou a překrystalován z acetonu. Bylo získáno 1,73 g látky (81,1 %) o t. t. 334 °C až 336 °C.A mixture of 2.32 g of 4-chloro-1,3-dimethyl-1H-pyrazolo (3,4-b) quinoline (10 mmol) and 23 ml of 1M hydrochloric acid was refluxed for 2 hours. After cooling the reaction mixture, aqueous ammonia was added to pH 8 and then neutralized with acetic acid. The insoluble material was aspirated, washed with water and recrystallized from acetone. 1.73 g (81.1%) of m.p. 334 ° C to 336 ° C were obtained.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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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 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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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) |
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 |
Publications (1)
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CS235182B1 true CS235182B1 (en) | 1985-05-15 |
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ID=5413268
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
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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 |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
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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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CS (6) | CS235167B1 (en) |
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1983
- 1983-09-09 CS CS658683A patent/CS235167B1/en unknown
- 1983-11-15 CS CS838460A patent/CS235183B1/en unknown
- 1983-11-15 CS CS838459A patent/CS235182B1/en unknown
- 1983-12-21 CS CS839743A patent/CS235188B1/en unknown
-
1984
- 1984-02-24 CS CS841309A patent/CS235198B1/en unknown
- 1984-02-24 CS CS841310A patent/CS235199B1/en unknown
Also Published As
Publication number | Publication date |
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CS235183B1 (en) | 1985-05-15 |
CS235188B1 (en) | 1985-05-15 |
CS235167B1 (en) | 1985-05-15 |
CS235198B1 (en) | 1985-05-15 |
CS235199B1 (en) | 1985-05-15 |
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