AT67948B - Process for the preparation of homologues and substitution products of 2-piperonylquinoline-4-carboxylic acid. - Google Patents
Process for the preparation of homologues and substitution products of 2-piperonylquinoline-4-carboxylic acid.Info
- Publication number
- AT67948B AT67948B AT67948DA AT67948B AT 67948 B AT67948 B AT 67948B AT 67948D A AT67948D A AT 67948DA AT 67948 B AT67948 B AT 67948B
- Authority
- AT
- Austria
- Prior art keywords
- homologues
- piperonylquinoline
- carboxylic acid
- substitution products
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000006467 substitution reaction Methods 0.000 title claims description 5
- IKVSQHOTFICZGX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(CC=3C=C4OCOC4=CC=3)=NC2=C1 IKVSQHOTFICZGX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- 229940081310 piperonal Drugs 0.000 claims description 2
- 229940107700 pyruvic acid Drugs 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KBBPTHUIJXSWFW-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-6-methylquinoline-4-carboxylic acid Chemical compound Cc1ccc2nc(Cc3ccc4OCOc4c3)cc(C(O)=O)c2c1 KBBPTHUIJXSWFW-UHFFFAOYSA-N 0.000 description 1
- BXJGDSAEIGHCPT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-8-methoxyquinoline-4-carboxylic acid Chemical compound COC=1C=CC=C2C(=CC(=NC12)CC1=CC=2OCOC2C=C1)C(=O)O BXJGDSAEIGHCPT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
Landscapes
- Seasonings (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Homologen und Substitutionsprodukten der 2-piperonylchinolin-4-karbons2ure.
Die in dem D. R. P. Nr. 244497 beschriebene 2-Piperonylchinolin-4-karbonsäure zeichnet sich vor der 2-Phenylchinolin-4-karbonsäure durch einen besseren Geschmack aus.
Man kann nun, wie gefunden wurde, zu völlig geschmackfreien Produkten gelangen, wenn man die Homologen oder Substitutionsprodukte des Anilins mit Piperonal und Brenztraubensäure nach den üblichen Methoden kondensiert.
Eine besondere Ausführungsform der dem vorliegenden Verfahren zugrunde liegenden Kondensationen ist bereits durch das Patent Nr. 63525 geschützt
EMI1.1
säure in alkoholischer Lösung mehrere Stunden am Kühler gekocht. Während des Kochens scheidet sich die 6-Methyl-2-piperonylchinolin-4-karbonsäure aus. Sie wird über das Natriumsalz gereinigt und schmilzt bei 246 bis 2470. Sie ist in Wasser unlöslich, löslich in heissem Alkohol.
EMI1.2
säure in alkoholischer Lösung mehrere Stunden gekocht. Die sich ausscheidende 8-Methoxy- -2-piperonylchinolin-4-karbonsäurewirdzweimalausalkalischerLösungdurchSäuregefällt und aus verdünntem alkohl umkristallisiert. Die Verbindung ist unlöslich in Wasser, löslich in Alkohol und. Alkalien.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of homologues and substitution products of 2-piperonylquinoline-4-carboxylic acid.
The 2-piperonylquinoline-4-carboxylic acid described in D.R.P. No. 244497 is distinguished from the 2-phenylquinoline-4-carboxylic acid by a better taste.
As has been found, it is now possible to obtain completely tasteless products if the homologues or substitution products of aniline are condensed with piperonal and pyruvic acid by the usual methods.
A special embodiment of the condensations on which the present process is based is already protected by patent no. 63525
EMI1.1
acid boiled in an alcoholic solution for several hours on the cooler. The 6-methyl-2-piperonylquinoline-4-carboxylic acid separates out during boiling. It is purified over the sodium salt and melts at 246 to 2470. It is insoluble in water, soluble in hot alcohol.
EMI1.2
acid boiled in alcoholic solution for several hours. The 8-methoxy--2-piperonylquinoline-4-carboxylic acid which precipitates is acid-precipitated twice from alkaline solution and recrystallized from dilute alcohol. The compound is insoluble in water, soluble in alcohol and. Alkalis.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE67948X | 1912-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT67948B true AT67948B (en) | 1915-02-10 |
Family
ID=5634174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT67948D AT67948B (en) | 1912-07-08 | 1913-06-27 | Process for the preparation of homologues and substitution products of 2-piperonylquinoline-4-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT67948B (en) |
-
1913
- 1913-06-27 AT AT67948D patent/AT67948B/en active
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