PL751B1 - Method for producing oxyphenylquinoline bicarbonate acid and its derivatives. - Google Patents
Method for producing oxyphenylquinoline bicarbonate acid and its derivatives. Download PDFInfo
- Publication number
- PL751B1 PL751B1 PL751A PL75120A PL751B1 PL 751 B1 PL751 B1 PL 751B1 PL 751 A PL751 A PL 751A PL 75120 A PL75120 A PL 75120A PL 751 B1 PL751 B1 PL 751B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- derivatives
- producing
- oxyphenylquinoline
- parts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- MQMWPBBDMIYYMI-UHFFFAOYSA-N 2-aminophenylglyoxylic acid Chemical compound NC1=CC=CC=C1C(=O)C(O)=O MQMWPBBDMIYYMI-UHFFFAOYSA-N 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 2
- 229940107700 pyruvic acid Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- JIPUGCBCIYYRSB-UHFFFAOYSA-N 3-phenylquinoline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 JIPUGCBCIYYRSB-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
Description
Znaleziono, ze przez kondensacje 'kwasu wy, zwiazek cenny przy leczeniu chorób ar- acetosalicylowego (GOCH3 — OH —COOH= tretyczmo reumatycznych. Przemiana tych = f: 2 :1) z kwasem izatynowym otrzymuje zwiazków odbywa sie wedle wzoru nastepu- sie kwas oksyfenylochinolino-dwukarbono- jacego: CO — COOH A/ V\ + NHa CH3 CO COH / - oh C —COOH A/ \H i COOH / "- OH + '2H20 Nowy zwiazek nie rozpuszcza sie w wo¬ dzie i w ligroinie wcale, slabo w alkoholu i w alkoholu metylowym. Otrzymuje sie go, jako zóltawy proszek, który topi sie przy 283—284°, rozkladajac sie przytem. Tworzy on sól dwusodowa, której rozczym ma smak slodki i zabarwiony zostaje na zólto przez dodanie lugu sodowego.Znaleziono nadto, ze mozna otrzymac ten sam kwas oksyfenylochinolinodwukarbono- wy przez nagrzewanie kwasu p-aldehydo-sa- • licylowego z anilina i kwasem pyrogrono- wym w rozczynie alkoholowym.Mozna równiez wytwarzac pochodne kwa¬ su oksyfenilochinolinodwukarbonowego, bar¬ dzo do tego ostatniego podobne, przez uzyciezamiast aniliny jej homologów albo pochod¬ nych, a zamiast kwasu acetosalicylowego, jego homologów w rodzaju np. kwasu aceto- o-kresotyinowego, albo aceto-rni-kresotynowe- go, albo toz zamiast kwasu iz-atynowego, je¬ go pochodnych, jak np. kwasu metyleno dwuoksyiziatynowego.Przyklady. 1. Do rozczyinu kwasu izatynowego, któ¬ ry powstal z rozpuszczenia 147 czesci iza- tyny w 600 czesciach 33% lugu potasowego, dodaje sie 180 czesci kwasu acetoisalicylo- wego i ogrzewa sie ten rozczyn na; lazni wodnej. Z rozczynu stracony kwasem solnym wypada kwas oksyfenylochinolLnodwukarbo- nowy, który sie nastepnie odfiltrowuje i przemywa cieplym alkoholem; ewentualnie moze on byc oczyszczony przez krystalizacje jego soli dwusodowej lub eteru dwuetylo- wego o punkcie topliwosci 103°, które moz¬ na otrzymac w sposób znany. 2. 166 czesci p-aldehydokwasu salicylo¬ wego rozpuszcza sie z 93 'Czesciami aniliny w 1000 czesciach alkoholu. Do rozczynu po¬ wstajacego zwiazku dodaje sie 88 czesci kwasu pyrogronowego i nagrzewa w ciagu 3—4 godzin az do wrzenia; po oddestylowa¬ niu alkoholu, rozpuszczamy osad w rozczy- nie wody, i z rozczynu alkalicznego zostaje kwas fenylochinolinokairbonowy stracony przez dodanie kwasu solnego. Dla otrzyma¬ nia zwiazku chemicznie czystego nalezy po¬ stapic, jak podane w przykladzie 1. PL PLIt has been found that through condensation of acid, a compound valuable in the treatment of aracetalicylic diseases (GOCH3 - OH —COOH = tretic rheumatic diseases. -dicarbonate: CO - COOH A / V \ + NHa CH3 CO COH / - oh C —COOH A / \ H and COOH / "- OH + '2H 2 O The new compound does not dissolve in water and ligroin at all, poorly in alcohol and methyl alcohol, it is obtained as a yellowish powder which melts at 283 ° -284 ° and decomposes in this case. It forms a disodium salt, the diluent of which has a sweet taste and is colored yellow by adding sodium liquor. that the same oxyphenylquinoline dicarboxylic acid can be obtained by heating p-aldehyde salicylic acid with aniline and pyrogronic acid in an alcoholic solution. It is also possible to produce oxyphenylquinoline dicarboxylic acid derivatives, very similar to the latter, by using Instead of aniline, its homologues or derivatives, and instead of acetalicylic acid, its homologues such as aceto-cotinic acid or aceto-cotinic acid, or tois instead of isatinic acid, its derivatives, such as e.g. methylene dioxyisiatinic acid. 1. 180 parts of acetoisalicylic acid are added to the isatinic acid solution, which is formed by dissolving 147 parts of isatin in 600 parts of 33% potassium liquor, and heating this solution; water bath. Oxyphenylquinol-dicarboic acid is lost from the solution, lost with hydrochloric acid, which is then filtered off and washed with warm alcohol; it may optionally be purified by crystallization of its disodium salt or diethyl ether having a melting point of 103 °, which can be obtained in a known manner. 2. 166 parts of p-aldehyde salicylic acid is dissolved with 93 'parts of aniline in 1000 parts of alcohol. 88 parts of pyrogronic acid are added to the resulting solution and heated for 3 or 4 hours until boiling; after distilling off the alcohol, we dissolve the precipitate in a dilution of water, and the alkaline solution is left with phenylquinoline carboxic acid lost by adding hydrochloric acid. To obtain a chemically pure compound, follow the steps given in example 1. PL PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL751B1 true PL751B1 (en) | 1924-10-31 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU718009A3 (en) | Method of producing 1-nitro-9-alkylaminoalkylaminoacridines or salts thereof | |
| PL751B1 (en) | Method for producing oxyphenylquinoline bicarbonate acid and its derivatives. | |
| SU52430A1 (en) | The method of obtaining salts of alkyl-sulfuric acid N, N'-alkyl diacridyl-9-urea | |
| Bogert et al. | RESEARCHES ON QUINAZOLINES (TWENTY-FOURTH PAPER). ON OXALYL ANTHRANILIC COMPOUNDS AND QUINAZOLINES DERIVED THEREFROM. | |
| US2312032A (en) | Preparation of new therapeutically useful heterocyclic compounds | |
| US2098094A (en) | Water-soluble organic iodine compounds | |
| DE281010C (en) | ||
| US1917749A (en) | Sodium ortho-phenyl phenate and method of preparing same | |
| US1684920A (en) | Water-soluble organic compound of antimony and process of producing it | |
| US1842626A (en) | Iodo methane sulphonic acid and homologues thereof | |
| US1988758A (en) | Organic arsenic compound | |
| SU7960A1 (en) | The method of obtaining meso-amine-acridine and its derivatives | |
| US2602797A (en) | J-ambmo-lo-methyl | |
| Child | 90. The sulphonation of o-anisidine and aceto-o-anisidide | |
| US3745159A (en) | 2-carboxy-1-benzalimino-1,5-dimethyl-2-phenyl-3-pyrazolone,organic and inorganic derivatives thereof and process for producing the same | |
| Porritt | IV.—Arylseleninic acids | |
| SU186905A1 (en) | ||
| SU48323A1 (en) | Method for preparing 4-nitro-2-aminoanisole | |
| SU523900A1 (en) | Method for preparing 1thio-1,1-dioxide-isochroman derivatives | |
| Moudgill | CLXXVII.—2: 8-Tetramethyldiaminoacridine | |
| US2063865A (en) | Salts of acridinium bases and a process of preparing them | |
| SU23411A1 (en) | Method for producing mercury-substituted in the core of dimethoxybenzoic acid derivative | |
| CH143277A (en) | Process for the preparation of an isatin derivative | |
| SU1315454A3 (en) | Method for producing phenothiazine derivatives or their lower alkyl esters,or their additive salts with acids | |
| Kenyon et al. | CCCCVIII.—Investigations in the diphenyl series. Part IV. Halogenation of 4-aminodiphenyl |