AT61190B - Process for the preparation of 2-phenylquinoline-4-carboxylic acid. - Google Patents
Process for the preparation of 2-phenylquinoline-4-carboxylic acid.Info
- Publication number
- AT61190B AT61190B AT61190DA AT61190B AT 61190 B AT61190 B AT 61190B AT 61190D A AT61190D A AT 61190DA AT 61190 B AT61190 B AT 61190B
- Authority
- AT
- Austria
- Prior art keywords
- phenylquinoline
- carboxylic acid
- preparation
- acetophenone
- acid
- Prior art date
Links
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von 2-Phenylchinolin-4-karbonsäure.
1m "Journal für praktische Chemie" [2], 38, S. 583, ist oine Bildungsart der 2-Phenylchinolin-4-karbonsäure angegeben, die sich ohne jede Angabe der erhaltenen Ausbeute auf die Mitteilung beschrankt, dass die genannte Säure aus Azetophenon und Isatin- s. dure in ziemlich starker alkoholischer Kalilauge erhältlich ist. Diese Notiz ist später ("Journal fur praktische Chemi" [2], 56, S. 293) dahin erweitert worden, dass man bei Anwendung von etwa 2 Molekülen Azetophenon auf 1 Molekül Isatin in wässerig
EMI1.1
1 Molekül Azetophenon der Heaktton völlig entgeht und nicht einmal unverändert wieder- swonnen werden kann, da sich bei der Kondensation harzigt'Produkte bilden.
Es wurde nun gefunden, dass man die Ausbeute an 2-Phenylchinolin-4-karbonsäure erheblich steigern kann, wenn man an Stelle eines Überschusses nur die etwa berechnete
EMI1.2
stand in Wasser gelöst und aus der nitrierten Lösung durch Zugabe dt'r berechneten Menge verdünnter Salzsäure die 2-Phenylchinolin-4-karbonsäure abgeschieden. Man erhält @o eine Ausbeute von etwa 90 . reiner Säure, die nach einmaligem Umlösen aus Alkohol den Schmelzpunkt 208 zeigt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of 2-phenylquinoline-4-carboxylic acid.
In the "Journal for practical chemistry" [2], 38, p. 583, a type of formation of 2-phenylquinoline-4-carboxylic acid is given, which is limited to the information that the acid mentioned from acetophenone and without any indication of the yield obtained Isatin- s. dure is available in fairly strong alcoholic potassium hydroxide solution. This note was later extended ("Journal fur Praxis Chemi" [2], 56, p. 293) to the effect that when about 2 molecules of acetophenone are used for 1 molecule of isatin in aqueous
EMI1.1
1 molecule of acetophenone which Heaktton completely escapes and cannot even be recovered unchanged, since resinous products are formed during condensation.
It has now been found that the yield of 2-phenylquinoline-4-carboxylic acid can be increased considerably if, instead of an excess, only the calculated amount
EMI1.2
was dissolved in water and the 2-phenylquinoline-4-carboxylic acid was deposited from the nitrated solution by adding the calculated amount of dilute hydrochloric acid. A yield of about 90 is obtained. pure acid, which has a melting point of 208 after being dissolved once from alcohol.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE61190X | 1912-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT61190B true AT61190B (en) | 1913-09-10 |
Family
ID=5630810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT61190D AT61190B (en) | 1912-05-21 | 1912-08-30 | Process for the preparation of 2-phenylquinoline-4-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT61190B (en) |
-
1912
- 1912-08-30 AT AT61190D patent/AT61190B/en active
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