DE270487C - - Google Patents
Info
- Publication number
- DE270487C DE270487C DENDAT270487D DE270487DA DE270487C DE 270487 C DE270487 C DE 270487C DE NDAT270487 D DENDAT270487 D DE NDAT270487D DE 270487D A DE270487D A DE 270487DA DE 270487 C DE270487 C DE 270487C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- pyrazolone
- dimethyl
- alcohol
- acetonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N Chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000001035 methylating Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE/12^. GRUPPECLASS / 12 ^. GROUP
Patentiert im Deutschen Reiche vom 28. November 1912 ab. Patented in the German Empire on November 28, 1912.
Es wurde gefunden, daß man zu in Stellung 2 oder 3 antipyrinsubstituierten Chinolin-4-carbonsäuren gelangt, wenn man i-Phenyl-2 · 3-dimethyl-4:-aceto-5-pyrazolon oder dessen Homologen mit Isatin in alkalischer Lösung in Reaktion bringt. Diese neuen Verbindungen, welche 'die Wirkung des i-Phenyl-2 · 3-dimethyl-5-pyrazolons mit der der Chinolin-4-carbonsäuren vereinigen, finden therapeutische Anwendung.It has been found that quinoline-4-carboxylic acids which are antipyrine-substituted in the 2 or 3 position can be obtained obtained when i-phenyl-2 · 3-dimethyl-4: -aceto-5-pyrazolone or its Bringing homologues with isatin in alkaline solution in reaction. These new connections which 'the effect of the i-phenyl-2 · 3-dimethyl-5-pyrazolons with that of the quinoline-4-carboxylic acids unite, find therapeutic application.
I. 50 g Isatin werden in 300 ecm 15 prozentiger Kalilauge gelöst und mit 100 g i-Phenyl-3-methyl-2 · 3-dimethyl-4-aceto-5-pyrazolon 24 Stunden auf dem Wasserbad erwärmt. Hierauf wird auf die Hälfte des ursprünglichen Volumens eingedampft und das nicht in Reaktion getretene i-Phenyl-2 · 3-dimethyl-4-aceto-5-pyrazolon mit Chloroform ausgezogen. Aus der wäßrigen Lauge fällt beim Abkühlen das Kaliumsalz der 2-Antipyrylchino-]in-4-carbonsäure aus. Dieses wird abgesaugt, in Wasser gelöst und mit der äquivalenten Menge Salzsäure ■ versetzt. Die freie Säure scheidet sich dann als Kristallbrei aus. Nach dem Umkristallisieren aus Alkohol schmilzt die 2-Antipyrylchinolin-4-carbonsäure bei 266 bis 268 °. In Alkalien ist sie leicht löslich; in verdünnten Säuren löst sie sich beim Erwärmen. I. 50 g of isatin become 15 percent in 300 ecm Dissolved potassium hydroxide solution and with 100 g of i-phenyl-3-methyl-2 · 3-dimethyl-4-aceto-5-pyrazolone Warmed on the water bath for 24 hours. Then it is reduced to half of the original Evaporated in volume and the unreacted i-phenyl-2 · 3-dimethyl-4-aceto-5-pyrazolone extracted with chloroform. The potassium salt of 2-antipyrylchino-] yn-4-carboxylic acid falls from the aqueous alkali on cooling the end. This is sucked off, dissolved in water and with the equivalent Amount of hydrochloric acid added. The free acid then separates out as a crystal pulp. To recrystallization from alcohol melts the 2-antipyrylquinoline-4-carboxylic acid at 266 up to 268 °. It is easily soluble in alkalis; in dilute acids it dissolves when heated.
II. 30 g Isatin werden in go g Kalilauge von 40 Prozent gelöst, mit 60 g I-Phenyl-2 · 3-dimethyl-4-acetonyl - 5 - pyrazolon in 1500 ecm Alkohol versetzt und 24 Stunden am Rückflußkühler gekocht. ·■ Hierauf wird der Alkohol abdestilliert und dem Rückstand das unveränderte i-Phenyl-2 · 3-dimethyl-4-acetonyl-5-pyrazolon durch Ausschütteln mit Essigester entzogen. Das Kaliumsalz der Methylantipyrylcbinolin - 4 - carbonsäure kristallisi ert bei genügender Konzentration leicht; es wird abgesaugt und mit Alkohol und Äther gewaschen. Die freie Säure, aus dem Kaliumsalz mit der berechneten Menge Mineralsäure abgeschieden und aus Alkohol umkristallisiert, schmilzt bei 238 bis 239 °. Ihrer Konstitution nach kann diese Säure ebensowohl die 2-Methyl-3-antipyrylchinolin-4-carbonsäure als auch die isomere 2 - Methylantipyrylchinolin^-carbonsäure sein.II. 30 g of isatin are dissolved in 40 percent g of potassium hydroxide solution with 60 g of I-phenyl-2 · 3-dimethyl-4-acetonyl - 5 - pyrazolone in 1500 ecm alcohol and 24 hours on the reflux condenser cooked. · ■ The alcohol is then distilled off and the unchanged from the residue i-Phenyl-2 · 3-dimethyl-4-acetonyl-5-pyrazolone by shaking with ethyl acetate withdrawn. The potassium salt of methylantipyrylcbinoline-4-carboxylic acid crystallizes easy with sufficient concentration; it is suctioned off and washed with alcohol and ether. The free acid, from the potassium salt with the calculated amount of mineral acid deposited and recrystallized from alcohol, melts at 238 to 239 °. Your constitution This acid can also be 2-methyl-3-antipyrylquinoline-4-carboxylic acid as well as the isomeric 2 - methylantipyrylquinoline ^ -carboxylic acid be.
Das oben erwähnte, noch nicht beschriebene i-Phenyl-2 ·The above-mentioned, not yet described i-phenyl-2 ·
CH3 CCH 3 C
C6H5-NC 6 H 5 -N
-COCH11 -COCH 11
COCO
5555
6060
erhält man durch Einwirkung von Acetylchlorid auf 1-Phenyl-2 · 3-dimethyl-5-pyrazolon in Gegenwart von Aluminiumchlorid. Es bildet farblose Kristalle vom Schmelzpunkt 150 bis 151°; in heißem Wasser, in Alkohol und in Chloroform ist es leicht löslich. Die wäßrige Lösung wird durch Eisenchlorid rot gefärbt.obtained by the action of acetyl chloride on 1-phenyl-2 · 3-dimethyl-5-pyrazolone in the presence of aluminum chloride. It forms colorless crystals with a melting point 150 to 151 °; in hot water, in alcohol and it is easily soluble in chloroform. The aqueous solution turns red due to ferric chloride colored.
lonlon
ι-Phenyl-2 · s-dimetyl^-acetonyl-s-pyrazo-ι-phenyl-2 · s-dimetyl ^ -acetonyl-s-pyrazo-
CH9-NCH 9 -N
C.ff«. W|iC.ff «. W | i
4j C · C H2' C 0 · C H3 CO 4j C • C H2 'C 0 • CH 3 CO
gewinnt man durch Methylieren von i-Phenyl-3-methyl-4-acetonyl-5-pyrazolon. Letzteres entsteht aus ι - Phenyl-3-methyl-5-pyrazolonis obtained by methylating i-phenyl-3-methyl-4-acetonyl-5-pyrazolone. The latter arises from ι - phenyl-3-methyl-5-pyrazolone
. beim Behandeln mit Chloraceton und Natronlauge. Das i-Phenyl-2 . 3-dimethyl-4-acetonyl-5-pyrazolon schmilzt bei 87 °; in Wasser sowie den meisten organischen Lösungsmitteln ist es leicht löslich. Mit Eisenchlorid färbt sich die wäßrige Lösung rot.. when treating with chloroacetone and sodium hydroxide solution. The i-phenyl-2. 3-dimethyl-4-acetonyl-5-pyrazolone melts at 87 °; it is easily soluble in water and most organic solvents. Stains with ferric chloride the aqueous solution turns red.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE270487C true DE270487C (en) |
Family
ID=527227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT270487D Active DE270487C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE270487C (en) |
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0
- DE DENDAT270487D patent/DE270487C/de active Active
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