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 PDF

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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
pyrazolo
dihydro
oxo
preparation
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CS838459A
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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 CS838459A priority Critical patent/CS235182B1/en
Publication of CS235182B1 publication Critical patent/CS235182B1/en

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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)

PREDMETSUBJECT Způsob přípravy 4,9-dihydro-l,3-dimethyl-4-oxo-lH-pyrazolo( 3,4-b) chinolínu, vyznačující se tím, že se 4-chlor-l,3-dímethyl-lH-pyVYNALEZU razolo(3,4-b)chinolin hydrolyzuje varem s 0,1 M až 5 M kyselinou chlorovodíkovou, výhodně s 1 M kyselinou chlorovodíkovou.A process for the preparation of 4,9-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo (3,4-b) quinoline, characterized in that the 4-chloro-1,3-dimethyl-1H-pyrimidine is Razolo (3,4-b) quinoline is hydrolyzed by boiling with 0.1 M to 5 M hydrochloric acid, preferably 1 M hydrochloric acid.
CS838459A 1983-09-09 1983-11-15 Preparation of 4,9-dihydro-1,3-dinityl-4-oxo-1H-pyrazolo (3,4-b) -quinoline CS235182B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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)

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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

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CS235182B1 true CS235182B1 (en) 1985-05-15

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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

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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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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
CS235198B1 (en) 1985-05-15
CS235199B1 (en) 1985-05-15

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