CH81056A - Process for the preparation of 2-phenylquinoline-4-carboxylic acid allyl ester - Google Patents
Process for the preparation of 2-phenylquinoline-4-carboxylic acid allyl esterInfo
- Publication number
- CH81056A CH81056A CH81056A CH81056DA CH81056A CH 81056 A CH81056 A CH 81056A CH 81056 A CH81056 A CH 81056A CH 81056D A CH81056D A CH 81056DA CH 81056 A CH81056 A CH 81056A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylquinoline
- carboxylic acid
- alcohol
- ester
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 2-phenylquinoline-4-carboxylic acid allyl ester Chemical class 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- AFHGMYUEOXZDBM-UHFFFAOYSA-N 2-phenylquinoline-4-carbonyl chloride Chemical compound N=1C2=CC=CC=C2C(C(=O)Cl)=CC=1C1=CC=CC=C1 AFHGMYUEOXZDBM-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 2-Plienylchinolin-4-earbonsäui#eallylester. Es wurde gefunden, dass man zum Allyl- ester der 2-Phenylchinolin-4-carbonsäure ge langen kann, wenn man die 2-Phenylchinolin- 4-carbonsäure mitAlly lverbindungen behandelt.
Es eignen sich hierzu sämtliche zur Ver- esterung von Säuren bekannten Methoden. Man kann zum Beispiel die Salze der 2-Phenyl- chinolin-4-oarbonsäure mit Allyllialogenid in geeigneten Lösungsmitteln umsetzen oder in eine allylalkoholische Lösung der 2-Phenyl- chinolin-4-carborisäure trockenes Salzsäuregas einleiten oder die genannte Lösung mit wenig .
konzentrierter Schwefelsäure erhitzen oder 2-Phenylchinolin-4-carborisäurechlorid mit Al- lylalkohol umsetzen usw.
Der 2-Phenylchinolin-4-carbonsäureallyl- ester besitzt vor der freien Säure unter an derem den Vorzug völliger Geschmacksfrei heit und weist die spezifisch harnsäurelösende Wirkung der 2-Phenylchinolin-4-cai-borisäure in bedeutend gesteigertem Masse auf, während eine solche Steigerung bei den entsprechenden Alkylestern nicht vorhanden ist.
Er siedet im Vakuum (15 mm) bei 260 und schmilzt bei 30 . Er kristallisiert aus Alkohol in langen Nadeln, ist in Wasser unlöslich, in Alkohol, Äther, Aceton und Olen leicht löslich. Das Chlorhydrat bildet, aus starkem Alkohol umkristallisiert, kleine zitronengelbe Nädelchen vom Schmelzpunkte 145-147 : Es ist unlöslich in Äther, leicht löslich in heissem Alkohol. Versetzt man dasselbe mit Wasser, so tritt momentan Spaltung in Ester und Salzsäure ein. Das Chlorhydrat besitzt einen schwach süsslichen Geschmack.
<I>Beispiel</I> r: 100 gr 2-phenylchinolin-4-carborisaures Natrium werden in 500 em3 Aceton gelöst, auf dem Wasserbade unter Rückflusskühlung zum Sieden erhitzt und dann 50 gr Allyl- bromid oder eine äquivalente Menge Allyl- chlorid zugesetzt. Nach beendigter Reaktion, zirka 6 Stunden, wird das Aceton und noch vorhandenes Allylierungsmittel im Vakuum abgedampft.
Der Rückstand wird im Scheide trichter mit Äther aufgenommen, die Äther lösung mit verdünnter Sodalösung und hierauf mit Wasser gewaschen und über Chlorcalcium getrocknet. Der freie tster wird zur Remigung im Vakuum destilliert, wobei derselbe bei 260 (15 mm) als schwach gelbliches Öl übergeht, welches bei Eiskühlung in Form von langen, schwach gelblich gefärbten Nadeln sich ausscheidet. Versetzt man die trockene Ätherlösung des Esters mit alkoholiseber Salzsäure, so fällt das Chlorhydrat als gelber, kristallinischer Niederschlag aus.
<I>Beispiel 2:</I> 250 gr 2=Phenylchinolin-4-carbonsäure wer den in einem Überschuss von Allylalkohol gelöst, am Rückflusskühler zum Sieden erhitzt und dann trockenes Salzsäuregas bis zur Sättigung eingeleitet.
Hierauf wird der Allyl- alkohol auf dem Wasserbade unter vermin dertem Druck abdestilliert und der Rück stand ausgeäthert. Zur Entfernung von Salz säure und überschüssiger 2-Phenylchinolin- 4-carbonsäure wird die Ätherlösung mit Soda und zuletzt mit Wasser gewaschen. Nach dem Abdestillieren des Äthers bleibt der Ester als dickes Öl zurück, welches auf dem Eise erstarrt.
<I>Beispiel 3</I> 270 gr 2-Phenylchinolin-4-carbonsäure- chlorid werden in Benzol gelöst und mit einem Überschuss von Allylalkohol auf dein Wasserbade erhitzt, bis keine Salzsäure mehr entweicht. Nach beendigter Reaktion werden Benzol und Allylalkohol im Vakuum ab destilliert und der Rückstand in Wasser ge- gossen. Die weitere Verarbeitung geschieht wie in Beispiel 2.
Process for the preparation of 2-plienylquinoline-4-carboxylic acid allyl ester. It has been found that the allyl ester of 2-phenylquinoline-4-carboxylic acid can be obtained if the 2-phenylquinoline-4-carboxylic acid is treated with allyl compounds.
All methods known for the esterification of acids are suitable for this purpose. For example, the salts of 2-phenyl-quinoline-4-carboxylic acid can be reacted with allyl halide in suitable solvents or dry hydrochloric acid gas can be introduced into an allyl alcoholic solution of 2-phenyl-quinoline-4-carboric acid or the solution mentioned with little.
Heat concentrated sulfuric acid or react 2-phenylquinoline-4-carboric acid chloride with allyl alcohol, etc.
The 2-phenylquinoline-4-carboxylic acid allyl ester has, among other things, the advantage of being completely free of taste over the free acid and has the specific uric acid-dissolving effect of 2-phenylquinoline-4-cai-boric acid to a significantly increased extent, while such an increase the corresponding alkyl esters is not present.
It boils in a vacuum (15 mm) at 260 and melts at 30. It crystallizes from alcohol in long needles, is insoluble in water and easily soluble in alcohol, ether, acetone and oils. Recrystallized from strong alcohol, the hydrated chlorine forms small lemon-yellow needles with a melting point of 145-147: it is insoluble in ether, easily soluble in hot alcohol. If water is added to it, cleavage into ester and hydrochloric acid occurs momentarily. The chlorine hydrate has a slightly sweet taste.
<I> Example </I> r: 100 grams of 2-phenylquinoline-4-carboric acid sodium are dissolved in 500 cubic meters of acetone, refluxed on a water bath and then 50 grams of allyl bromide or an equivalent amount of allyl chloride are added . After the reaction has ended, about 6 hours, the acetone and any allylating agent still present are evaporated off in vacuo.
The residue is taken up in the separating funnel with ether, the ether solution is washed with dilute soda solution and then with water and dried over calcium chloride. The free tster is distilled in vacuo to remove it, and at 260 (15 mm) it turns into a pale yellowish oil, which separates out in the form of long, pale yellowish needles when cooled with ice. If the dry ether solution of the ester is mixed with alcoholic hydrochloric acid, the hydrochloric acid precipitates out as a yellow, crystalline precipitate.
<I> Example 2: </I> 250 g 2 = phenylquinoline-4-carboxylic acid who dissolved in an excess of allyl alcohol, heated to boiling on the reflux condenser and then introduced dry hydrochloric acid gas until saturation.
The allyl alcohol is then distilled off on the water bath under reduced pressure and the residue is extracted with ether. To remove hydrochloric acid and excess 2-phenylquinoline-4-carboxylic acid, the ethereal solution is washed with soda and finally with water. After the ether has been distilled off, the ester remains as a thick oil, which solidifies on the ice.
<I> Example 3 </I> 270 g of 2-phenylquinoline-4-carboxylic acid chloride are dissolved in benzene and heated to the water bath with an excess of allyl alcohol until no more hydrochloric acid escapes. After the reaction has ended, benzene and allyl alcohol are distilled off in vacuo and the residue is poured into water. Further processing is carried out as in example 2.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH81056T | 1918-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH81056A true CH81056A (en) | 1920-06-01 |
Family
ID=4335237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH81056A CH81056A (en) | 1918-06-07 | 1918-06-07 | Process for the preparation of 2-phenylquinoline-4-carboxylic acid allyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH81056A (en) |
-
1918
- 1918-06-07 CH CH81056A patent/CH81056A/en unknown
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