DE416329C - Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulphonic acid - Google Patents
Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulphonic acidInfo
- Publication number
- DE416329C DE416329C DEF55136D DEF0055136D DE416329C DE 416329 C DE416329 C DE 416329C DE F55136 D DEF55136 D DE F55136D DE F0055136 D DEF0055136 D DE F0055136D DE 416329 C DE416329 C DE 416329C
- Authority
- DE
- Germany
- Prior art keywords
- water
- oxyquinoline
- iodo
- soluble
- bismuth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001622 bismuth compounds Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000243 solution Substances 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 150000001621 bismuth Chemical class 0.000 description 2
- -1 bismuth nitrate-mannitol Chemical compound 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- GSPKOLDTWNEPSI-UHFFFAOYSA-N 3-iodylquinoline-2-sulfonic acid Chemical compound I(=O)(=O)C=1C(=NC2=CC=CC=C2C=1)S(=O)(=O)O GSPKOLDTWNEPSI-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 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
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940049676 bismuth hydroxide Drugs 0.000 description 1
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Verfahren zur Darstellung einer in Wasser löslichen, komplexen Wismutverbindung der 7-Jod-8-oxychinolin-5-sulfosäure. Das Wismutsalz der 7-Jod-g-oxychinolin-5-sulfosäure ist in Wasser und Alkalien unlöslich und enthält das Wismut an die Sulfosäuregruppe gebunden.Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulfonic acid. The bismuth salt of 7-iodo-g-oxyquinoline-5-sulfonic acid is insoluble in water and alkalis and contains the bismuth bound to the sulfonic acid group.
Es wurde nun die überraschende Beobachtung gemacht, daß durch Umsetzung von 7-jod-8-oxychinolin-7-sulfosaürem Natrium mit Wismutnitrat-Mannit-Lösungen (v,-l. O. V a n i n o , Zeitschr, für anorg. Chemie 28, S. 21o [igoi]) oder mit Wismutnitratzuckerlösungen eine Wismutverbindung der jodoxychinolinsulfosäure in Form eines dauernd haltbaren, wasserlöslichen Nätriurnsalzes erhalten wird, das neutrale Reaktion aufweist und bei dem durch Alkalizusatz keine Ausscheidung von Wismuthydroxyd erfolgt. Die Bildung einer derartigen Verbindung ist überraschend, denn nach den Feststellungen von V a n i n owar vielmehr zu erwarten, daß durch Umsetzung von Wismutnitrat-Mannit-Lösungen mit Natriumsalzen von Säuren nur unlösliche Wismutsalze der Säuren entstehen (siehe V a n i n o a. a. O. S. 217). Wenn V a n i n o a. a. O. davon spricht, daß frisch dargestellte Wismutverbindungen der Salicylsäure und liampfersäure alkalilöslich seien, so hat er in späteren Arbeiten (vgl. z. B. Journal für prakt. Chemie N. F. Bd.7q. [19o6] S. 48) diese Bemerkung weder wiederholt noch experimentell gestützt, und Versuche der Erfinder haben die völlige Unlöslichkeit der betreffenden Verbindungen in Alkalien ergeben.The surprising observation has now been made that the reaction of 7-iodo-8-oxyquinoline-7-sulfosaürem sodium with bismuth nitrate-mannitol solutions (v, -l. O. V anino, Zeitschr, für anorg. Chemie 28, p 21o [igoi]) or with bismuth nitrate sugar solutions, a bismuth compound of iodoxyquinoline sulfonic acid is obtained in the form of a permanently stable, water-soluble nutrient salt which has a neutral reaction and in which the addition of alkali does not result in the excretion of bismuth hydroxide. The formation of such a compound is surprising, because according to the findings of V anino it was rather to be expected that only insoluble bismuth salts of the acids are formed by the reaction of bismuth nitrate-mannitol solutions with sodium salts of acids (see V anino op . Cit. P. 217) . When V anino, op. Cit., Speaks of the fact that freshly prepared bismuth compounds of salicylic acid and liampic acid are alkali-soluble, he has in later works (cf. e.g. Journal für Prakt. Chemie NF Vol.7q. [19o6] p. 48) this remark is neither repeated nor experimentally supported, and experiments by the inventors have shown the complete insolubility of the compounds in question in alkalis.
Die neue Verbindung enthält das Wismut in komplexer Form gebunden. Sie läßt sich aus der wäßrigen Lösung durch geeignete Fällungsmittel, wie Alkohol, Methylalkohol oder Aceton, in fester Form gewinnen. Sie soll zur Behandlung luetischer Erkrankungen Verwendung finden.The new compound contains the bismuth bound in a complex form. It can be removed from the aqueous solution by suitable precipitants, such as alcohol, Obtain methyl alcohol or acetone in solid form. She is said to be used to treat syphilis Diseases find use.
Beispiel i.Example i.
17,5g (i M01.) 7-Oxy-8-jodcliinolin-5-sulfosäure werden in 5o ccm 2-n-Natronlauge und ioo ccm Wasser gelöst und mit einer Mannitwismutnitratlösung nach O. V a n i n o , aus 8,3 g Wismutnitrat, q. g Mannit und 25 ccm Wasser bereitet, unter - Umrühren tropfenweise vers etzt.17.5 g (i M01.) 7-Oxy-8-iodoclinoline-5-sulfonic acid are dissolved in 50 ccm 2 N sodium hydroxide solution and 100 ccm of water and dissolved with a mannitol bismuth nitrate solution according to O. V a n i n o, from 8.3 g bismuth nitrate, q. g mannitol and 25 cc water, while stirring - added drop by drop.
Die gelbe klare Lösung, die neutrale Reaktion zeigt, wird in dünnem Strahl unter Rühren in 5oo ccm Alkohol einfließen gelassen. Es scheidet sich ein feiner flockiger gelber Niederschlag aus, der sich glatt mit neutraler Reaktion in Wasser löst. Wismutgehalt - 16,2o Prozent Bi. Beispiel 2.The yellow clear solution, which shows neutral reaction, is in thin The stream is poured into 500 cc of alcohol while stirring. It settles in fine fluffy yellow precipitate, which becomes smooth with a neutral reaction dissolves in water. Bismuth content - 16.2o percent Bi. Example 2.
8,7g 7-Jod-8-oxychinolin-5-sulfosäure werden in 25 ccm 2-n-N,atronlauge und 75 ccm Wasser gelöst und die klarfiltrierte Lösung mit einer Auflösung von 4,5,-, Wismutnitrat in 4,2g Mannose und to ccm Wasser unter Umrühren versetzt. Die klare dunkelbraune Lösung wird in dünnem Strahl unter Rühren in 3oo ccm Methylalkohol einfließen gelassen.8.7 g of 7-iodo-8-oxyquinoline-5-sulfonic acid are dissolved in 25 ccm of 2-nN, atronic liquor and 75 cc of water and the clear-filtered solution with a resolution of 4.5, bismuth nitrate in 4.2 g of mannose and to ccm of water was added while stirring. The clear, dark brown solution is poured into 300 cc of methyl alcohol in a thin stream with stirring.
Es fällt ein hellgelber, flockiger Niederschlag aus, der leicht in Wasser mit neutraler Reaktion löslich ist. Er enthält etwa 13 Prozent Wismut.A light yellow, flaky precipitate separates out, which is easily soluble in water with a neutral reaction. It contains about 13 percent bismuth.
Beispiel 3.Example 3.
8,7 g 7-Jod-8-oxychinolin-5-sulfosäure werden in 25 ccm 2-n-Natronlauge und 75 ccm Wasser gelöst und in die klarfiltrierte Lösung unter Rühren eine Lösung von ¢,2 g Wismutnitrat in 4,5 g Fructose und 8 ccm Wasser langsam zugegeben. Die dunkelbraune Lösung wird in dünnem Strahle in die vierfache Menge Alkohol einfließen gelassen.8.7 g of 7-iodo-8-oxyquinoline-5-sulfonic acid are dissolved in 25 ccm of 2N sodium hydroxide solution and 75 cc of water are dissolved and a solution is added to the clear-filtered solution while stirring of ¢, 2 g of bismuth nitrate in 4.5 g of fructose and 8 ccm of water were slowly added. the dark brown solution will pour into four times the amount of alcohol in a thin stream calmly.
Der entstehende hellgelbe Niederschlag ist klar in Wasser mit neutraler Reaktion löslich. Er enthält etwa 13 Prozent Wismut komplex gebunden.The resulting pale yellow precipitate is clearly soluble in water with a neutral reaction. It contains about 13 percent bismuth bound in a complex.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF55136D DE416329C (en) | 1923-12-18 | 1923-12-18 | Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulphonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF55136D DE416329C (en) | 1923-12-18 | 1923-12-18 | Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulphonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE416329C true DE416329C (en) | 1925-07-16 |
Family
ID=7107576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF55136D Expired DE416329C (en) | 1923-12-18 | 1923-12-18 | Process for the preparation of a water-soluble, complex bismuth compound of 7-iodo-8-oxyquinoline-5-sulphonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE416329C (en) |
-
1923
- 1923-12-18 DE DEF55136D patent/DE416329C/en not_active Expired
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