DE279195C - - Google Patents
Info
- Publication number
- DE279195C DE279195C DENDAT279195D DE279195DA DE279195C DE 279195 C DE279195 C DE 279195C DE NDAT279195 D DENDAT279195 D DE NDAT279195D DE 279195D A DE279195D A DE 279195DA DE 279195 C DE279195 C DE 279195C
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- aniline
- acid
- aminobenzaldehyde
- solution
- 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
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- LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 12
- 229940107700 Pyruvic Acid Drugs 0.000 claims description 6
- 230000001476 alcoholic Effects 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims description 3
- VATYWCRQDJIRAI-UHFFFAOYSA-N 4-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 claims description 3
- YTRMTPPVNRALON-UHFFFAOYSA-N Cinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- -1 amino compound Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- QMQXAQUBDPFOSS-UHFFFAOYSA-N 2-phenyl-1H-quinoline-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C=CC1(C(=O)O)C1=CC=CC=C1 QMQXAQUBDPFOSS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000036826 Excretion Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 208000000913 Kidney Calculi Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Trioxopurine Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- 229940116269 Uric Acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910000460 iron oxide Inorganic materials 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch Reduktion der 2 · 2'-, 2 · 3'- oder 2 · 4'-Nitrophenylchinolin-4-carbonsäure gelangt man zu den entsprechenden Aminoverbindungen, welche für ähnliche therapeutische Zwecke Verwendung finden sollen wie die 2-Phenylchinolin-4-carbonsäure selbst. Vor dieser besitzen die neuen Verbindungen den Vorzug, daß sie entweder eine weit geringere Harnsäureausscheidung herbeiführen oder diese ganz unbeeinflußt lassen. Sie werden daher vorteilhaft besonders in solchen Fällen verwendet, wo bei den Patienten Neigung zu Nierensteinbildungen vorhanden ist, die Anwendung der 2 - Phenylchinolin - 4 - carbonsäure also kontraindiziert erscheint.By reducing the 2x2'-, 2x3'- or 2x4'-nitrophenylquinoline-4-carboxylic acid, one arrives at the corresponding amino compounds, which are to be used for similar therapeutic purposes as the 2-phenylquinoline-4-carboxylic acid itself The advantage of the new compounds over this is that they either induce a much lower uric acid excretion or leave this completely unaffected. They are therefore used particularly advantageously in those cases where the patient is prone to kidney stone formation, so the use of 2-phenylquinoline-4-carboxylic acid appears contraindicated.
i. Darstellung der 2 · 2'-Aminophenylchin ο Ii η-4-c ar bon säure.i. Representation of the 2 · 2'-aminophenylquin ο Ii η-4-carbon acid.
30 g 2 · 2'-Nitrophenylchinolin-4-carbonsäure (Schmelzpunkt 253 bis 255 °; am zweckmäßigsten dargestellt durch allmählichen Zusatz von Brenztraubensäure zu einer siedenden alkoholischen Lösung von o-Nitrobenzaldehyd und Anilin) werden in wäßrigem, überschüssigem Ammoniak gelöst und in eine mit überschüssigemAmmoniak versetzte Lösung von 250 g Ferrosulfat in 1000 ecm Wasser eingetragen. Es wird unter Umschütteln 1 bis 2 Stunden auf dem Wasserbad erwärmt, von ausgeschiedenen Eisenoxyden abfiltriert und das aus der ammoniakalischen Lösung mit Salzsäure gefällte Produkt aus wäßrigem Alkohol umkristallisiert. Die neue Verbindung, die einen Schmelzpunkt von 225 bis 226 ° hat, ist löslieh in Säuren und Alkalien, schwer löslich in kochendem Wasser, leichter löslich in heißem Alkohol und Essigester, sehr schwer löslich in Äther.30 g of 2 · 2'-nitrophenylquinoline-4-carboxylic acid (melting point 253 to 255 °; most suitable represented by the gradual addition of pyruvic acid to a boiling alcoholic Solution of o-nitrobenzaldehyde and aniline) are in aqueous, excess Dissolved ammonia and in a solution of 250 g mixed with excess ammonia Ferrous sulfate added to 1000 ecm of water. It will be shaken for 1 to 2 hours warmed up on the water bath, filtered off the precipitated iron oxides and that off the ammoniacal solution with hydrochloric acid precipitated product recrystallized from aqueous alcohol. The new compound, which has a melting point of 225 to 226 °, is soluble in acids and alkalis, sparingly soluble in boiling water, more easily soluble in hot water Alcohol and ethyl acetate, very sparingly soluble in ether.
2. Darstellung der 2 · 3'-Aminophenylchinolin-4-carbonsäure. 2. Preparation of the 2x3'-aminophenylquinoline-4-carboxylic acid.
30. g 2 · s'-Nitrophenylchmolin^-carbonsäure (Schmelzpunkt 260 ° unkorrigiert; analog dargestellt wie die entsprechende o-Verbindung) werden in eine Lösung von 60 g kristallisiertem Schwefelnatrium in 300 ecm Wasser eingetragen. Hierauf wird 1 bis 2 Stunden auf dem Wasserbad erwärmt, angesäuert, von ausgeschiedenem Schwefel abfiltriert und aus dem salzsauren Filtrat die Aminoverbindung mit Natriumacetatlösung ausgefällt. Aus Wasser umkristallisiert, hat die Base den Schmelzpunkt 227 bis 228° (unkorrigiert). Sie ist leicht löslich in Alkalien und Säuren sowie in kochendem Wasser.30. g of 2 · s'-nitrophenylchmoline ^ -carboxylic acid (Melting point 260 ° uncorrected; represented analogously to the corresponding o-compound) are introduced into a solution of 60 g of crystallized sodium sulphide in 300 ecm of water. Then 1 to 2 hours on the water bath is heated, acidified, from The precipitated sulfur is filtered off and the amino compound is removed from the hydrochloric acid filtrate precipitated with sodium acetate solution. Recrystallized from water, the base has the Melting point 227 to 228 ° (uncorrected). It is easily soluble in alkalis and acids as well in boiling water.
3. Die 2 · 4'-Aminophenylchinolin-4-carbonsäure wird analog hergestellt aus der entsprechenden p-Nitro verbindung vom Schmelzpunkt 255 bis 256 °, die man auch durch unmittelbare Nitrierung der 2-Phenylchinolincarbonsäure erhalten kann. Die p-Äminoverbindung bildet ein rotes, feinsandiges Pulver. Es sintert gegen 193 bis 194 ° unter Schmelzerscheinung,- wird wieder fest und schmilzt dann bei 273 °. Die Verbindung ist leicht löslich in3. The 2 · 4'-aminophenylquinoline-4-carboxylic acid is prepared analogously from the corresponding one p-nitro compound with a melting point of 255 to 256 °, which can also be obtained by direct Nitration of 2-phenylquinolinecarboxylic acid can get. The p-amino compound forms a red, fine-sand powder. It sinters against 193 to 194 ° with the appearance of melting, - becomes solid again and then melts at 273 °. The compound is easily soluble in
Alkalien und Säuren, sehr schwer löslich in den meisten organischen Lösungsmitteln.Alkalis and acids, very sparingly soluble in most organic solvents.
Die Aminoverbindungen kann man auch in der Weise erhalten, daß man die betreffenden Aminobenzaldehyde, Anilin und Brenztraubensäure aufeinander in alkoholischer Lösung einwirken läßt. Man verfährt am zweckmäßigsten so, daß man Brenztraubensäure in eine siedende alkoholische Lösung des Kondensationsproduktes aus Anilin und dem betreffenden Aminobenzaldehyd einträgt und das Reaktionsgemisch noch einige Zeit weiter erhitzt.The amino compounds can also be obtained in such a way that the relevant Aminobenzaldehyde, aniline and pyruvic acid interact in alcoholic solution leaves. The most expedient procedure is to convert pyruvic acid into a boiling alcoholic solution of the condensation product of aniline and the relevant Aminobenzaldehyde enters and the reaction mixture is heated for some time.
4. 310 g p-Aminobenzaldehyd werden mit 24 g Anilin in alkoholischer siedender Lösung zur Benzylidenverbindung kondensiert, die berechnete Menge Brenztraubensäure eingetragen und die ausgeschiedene harzige Masse, welche völlig fest wird, aus Sodalösung umgefällt.4. 310 g of p-aminobenzaldehyde are added 24 g of aniline condensed in alcoholic boiling solution to the benzylidene compound, the calculated Amount of pyruvic acid entered and the excreted resinous mass, which becomes completely solid, precipitated from soda solution.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE279195C true DE279195C (en) |
Family
ID=535131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT279195D Active DE279195C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE279195C (en) |
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0
- DE DENDAT279195D patent/DE279195C/de active Active
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