CS235182B1 - Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation - Google Patents
Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation Download PDFInfo
- Publication number
- 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dimethyl
- pyrazolo
- dihydro
- oxo
- quinoline
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims abstract description 5
- SAAYKVOWLGPGDF-UHFFFAOYSA-N 1,3-dimethyl-9H-pyrazolo[3,4-b]quinolin-4-one Chemical compound CN1N=C(C2=C1NC1=CC=CC=C1C2=O)C SAAYKVOWLGPGDF-UHFFFAOYSA-N 0.000 title claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000009835 boiling Methods 0.000 claims abstract description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 4
- -1 4-chloro-1,3-dimethyl-1H-pyrimidine Chemical compound 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CLRNUDVGJVDYTG-UHFFFAOYSA-N 4-chloro-1,3-dimethylpyrazolo[3,4-b]quinoline Chemical compound C1=CC=C2C(Cl)=C3C(C)=NN(C)C3=NC2=C1 CLRNUDVGJVDYTG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LMBRFPRUZRLJAW-UHFFFAOYSA-N (5-amino-1,3-dimethylpyrazol-4-yl)-(2-fluorophenyl)methanone Chemical compound CC1=NN(C)C(N)=C1C(=O)C1=CC=CC=C1F LMBRFPRUZRLJAW-UHFFFAOYSA-N 0.000 description 1
- YCWUYQQRIHWNLH-UHFFFAOYSA-N 2-[(2,5-dimethylpyrazol-3-yl)amino]benzoic acid Chemical compound CN1N=C(C)C=C1NC1=CC=CC=C1C(O)=O YCWUYQQRIHWNLH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 present invention relates to a new method of preparation 4,9-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo- (3,4-b of quinoline characterized in that it is hydrolyses 4-bromo-1,3-dimethyl-1H-pyrazolo ( 3,4-b Jchiholine 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 |
|---|---|---|---|
| CS838459A CS235182B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS658683A CS235167B1 (en) | 1983-09-09 | 1983-09-09 | Substituted 4,9-dihydro-3-methyl-4-oxo-1h-pyrazolo-(3,4-b)quinolines and method of their production |
| CS838459A CS235182B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235182B1 true CS235182B1 (en) | 1985-05-15 |
Family
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-pyrazolo-(3,4-b)quinolines and method of their production |
| CS838459A CS235182B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS838460A CS235183B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-3,9-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS839743A CS235188B1 (en) | 1983-09-09 | 1983-12-21 | 4,9-dihydro-1-1(2,3-dihydroxypropyl)-3-methyl-4-oxo-1h-pyrazolo (3,4-b) quinoline and method of its preparation |
| CS841309A CS235198B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl)-1h-pyrazolo (3,4-b) quinolines and 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 (1)
| 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-pyrazolo-(3,4-b)quinolines and method of their production |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS838460A CS235183B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-3,9-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS839743A CS235188B1 (en) | 1983-09-09 | 1983-12-21 | 4,9-dihydro-1-1(2,3-dihydroxypropyl)-3-methyl-4-oxo-1h-pyrazolo (3,4-b) quinoline and method of its preparation |
| CS841309A CS235198B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl)-1h-pyrazolo (3,4-b) quinolines and 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 |
Country Status (1)
| Country | Link |
|---|---|
| CS (6) | CS235167B1 (en) |
-
1983
- 1983-09-09 CS CS658683A patent/CS235167B1/en unknown
- 1983-11-15 CS CS838459A patent/CS235182B1/en unknown
- 1983-11-15 CS CS838460A patent/CS235183B1/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 |
|---|---|
| CS235167B1 (en) | 1985-05-15 |
| CS235188B1 (en) | 1985-05-15 |
| CS235198B1 (en) | 1985-05-15 |
| CS235199B1 (en) | 1985-05-15 |
| CS235183B1 (en) | 1985-05-15 |
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