CH90412A - Process for the preparation of 2-phenylquinoline-4-carboxylic acid benzyl ester. - Google Patents
Process for the preparation of 2-phenylquinoline-4-carboxylic acid benzyl ester.Info
- Publication number
- CH90412A CH90412A CH90412DA CH90412A CH 90412 A CH90412 A CH 90412A CH 90412D A CH90412D A CH 90412DA CH 90412 A CH90412 A CH 90412A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- phenylquinoline
- preparation
- water
- soluble
- 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 benzyl ester Chemical compound 0.000 title description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 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 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 230000009967 tasteless effect Effects 0.000 claims description 2
- CGLYUMRYFOEGNE-UHFFFAOYSA-N 3-phenylquinoline-4-carboxylic acid Chemical compound C1=NC2=CC=CC=C2C(C(=O)O)=C1C1=CC=CC=C1 CGLYUMRYFOEGNE-UHFFFAOYSA-N 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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
- 229910021532 Calcite Inorganic materials 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 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
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical group O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2-Phenylchinolin-4-carbonsäurebenzylester. Es wurde gefunden, dass man zum Berr- zyle8ter der 2-Phertylchinolin-4-carbonsäure gelangen kann, weint mau die 2-Pheny lchino- lin-4-carbonsäure mit Benzylverbindungen behandelt. Es eignen sich hierzu sämtliche zur Ver- esterung voll Säuren bekannten Methoden.
Matt kann zum Beispiel die Salze der 2-Plreny 1- chirtolin-4-carbousäure mit Benzylhalogernd irr geeigneten Lösungsmitteln umsetzen oder in eine benzylalkoholische Lösung der 2-Phenyl- chinolin-4-carbonsäure trockenes Salzsäuregas einleiten oder die genannte Lösung mit wellig konzentrierter Schwefelsäure erhitzen oder 2=Phenylchinolin-4-carbonsäurechlor-id mit Ben- zylalkohol umsetzen.
- Der 2-Phenylchinofin-4-carborrsäLirebenzyl- ester besitzt vor der-freien Säure den Vorzug völliger Geschmacksfreiheit ürtd weist die spezifisch harnsäurelösenda Wirkung der 2-Pherrylchirrolin-4-carbonsäure in bedeutend gesteigertem Masse auf, während eilte solche Steigerung bei den Alkylestern nicht vor handen ist. Er bildet zitronengelbe Kristalle, die bei 77-78 schmelzen und in Wasser unlöslich, in Äther mässig und in Benzol und Neu leicht löslich sind.
Das Chlorhydrat bildet ein feines, gelbes, kristallinisches Pulver, welches in Wasser und Alkohol löslich, in Äther unlöslich ist. Beispiel <I>1:</I> <B>2,5</B> Teile 2-Pherrylchitrolin-4-car#honsattr-es Natrium, fein gepulvert, werden in 10 Teilen Aceton suspendiert und auf dem Wasserbade am Rückflusskühler zum Sieden erhitzt.- Dazu lässt malt unter Rühren allmählich 1,25 Teile Benzylchlorid zutropfen. Nach beendeter Reak tion, die ca. 20-24 Stunden dauert, wird das Aceton abdestilliert,
der Rückstand mit Wasser versetzt und mit einem indifferenten Lösungsmittel, wie Äther, Benzol ete. aus geschüttelt und getrennt. Die Üenzollösung wird hernach mehrmals mit verdünnter Soda lösung ausgeschüttelt, zuletzt mit Wasser neutral gewaschen und über Chlorcalcittm ge trocknet.
Durch Einleiten von trockenem Salzsäuregas in die Benzollösung erhält matt das Chlorhydrat des 2-Phenylchirrolirr-4-car- borrsäureberrzy lesters als feines, kristallinisches gelbes Pulver. Dasselbe wird in Alkohol ge löst, durch Zusatz von fester Soda zerlegt, vom ausgeschiedenen Kochsalz abfiltriert, worauf nach Einengen der Lösung der Ester auskristallisiert. Durch I:mkristallisieren aus Alkohol oder Äther wird derselbe rein erhalten.
<I>Beispiel 2</I> v,5 Teile 2-Pherrylchirrolin-4-car@bons"i,ur-e- chlcerid, 1, 2 Teile Benzylalkohol und 10 Teile Benzol oder Toluol werden im Olbad am Rückflusskühler während ea. 1b-20 Stunden zum Sieden erhitzt. Nach dein Erkalten wird die Reaktionsmasse mit Wasser und ver dünnter Sodalösurrg versetzt und gut durch geschüttelt.
Die abgetrennte Benzolschicht wird mehrmals mit verdünnter Sololösung ausgeschüttelt., zuletzt mit Wasser neutral gewaschen und über Chlorcalcium getrocknet.
Durch Einleiten von trockenem Salzsäure gas in die Benzollösung fällt das Chlorhydrat des Esters als feines, kristallinisches, gelbes Pulver aus, aus dem der Ester wie in Bei spiel 1 in Freiheit gesetzt wird.
Process for the preparation of 2-phenylquinoline-4-carboxylic acid benzyl ester. It has been found that one can get to the benzylic ester of 2-phertylquinoline-4-carboxylic acid by treating 2-phenylquinoline-4-carboxylic acid with benzyl compounds. All methods known for full acid esterification are suitable for this purpose.
Matt can, for example, react the salts of 2-plreny 1-chirtoline-4-carbous acid with benzyl halide in suitable solvents or introduce dry hydrochloric acid gas into a benzyl alcoholic solution of 2-phenyl-quinoline-4-carboxylic acid or heat the solution mentioned with wavy concentrated sulfuric acid or 2 = react phenylquinoline-4-carboxylic acid chlorid with benzyl alcohol.
- The 2-phenylquinofin-4-carborrsäLirebenzyl- ester has the advantage over the free acid that it is completely tasteless hand is. It forms lemon yellow crystals which melt at 77-78 and are insoluble in water, moderately soluble in ether and easily soluble in benzene and new.
The chlorine hydrate forms a fine, yellow, crystalline powder, which is soluble in water and alcohol, but insoluble in ether. Example <I> 1: </I> <B> 2.5 </B> parts of 2-Pherrylchitrolin-4-car # honsattr-es sodium, finely powdered, are suspended in 10 parts of acetone and refluxed on the water bath Heated to the boil.- To this, paint slowly lets 1.25 parts of benzyl chloride drop in while stirring. After the reaction, which lasts approx. 20-24 hours, the acetone is distilled off,
the residue is mixed with water and ete with an inert solvent such as ether, benzene. shaken off and separated. The Üenzoll solution is then shaken out several times with dilute soda solution, finally washed neutral with water and dried over chlorine calcite.
By introducing dry hydrochloric acid gas into the benzene solution, the chlorohydrate of the 2-phenylchirrolir-4-carborric acid ferric ester becomes matt as a fine, crystalline yellow powder. The same is dissolved in alcohol, broken down by the addition of solid soda, filtered off from the precipitated common salt, whereupon the ester crystallizes out after concentrating the solution. By crystallizing it from alcohol or ether it is obtained pure.
<I> Example 2 </I> v, 5 parts of 2-Pherrylchirrolin-4-car @ bons "i, ur-e-chlcerid, 1, 2 parts of benzyl alcohol and 10 parts of benzene or toluene are in the oil bath on the reflux condenser during ea. Heated to the boil for 1b-20 hours. After cooling, the reaction mass is mixed with water and dilute soda solution and shaken well.
The separated benzene layer is shaken out several times with dilute solvent solution, finally washed neutral with water and dried over calcium chloride.
By introducing dry hydrochloric acid gas into the benzene solution, the hydrochloride of the ester precipitates out as a fine, crystalline, yellow powder, from which the ester is released as in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH90412T | 1919-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH90412A true CH90412A (en) | 1921-09-01 |
Family
ID=4347651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90412D CH90412A (en) | 1919-07-03 | 1919-07-03 | Process for the preparation of 2-phenylquinoline-4-carboxylic acid benzyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH90412A (en) |
-
1919
- 1919-07-03 CH CH90412D patent/CH90412A/en unknown
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