DE129452C - - Google Patents
Info
- Publication number
- DE129452C DE129452C DE1900129452D DE129452DA DE129452C DE 129452 C DE129452 C DE 129452C DE 1900129452 D DE1900129452 D DE 1900129452D DE 129452D A DE129452D A DE 129452DA DE 129452 C DE129452 C DE 129452C
- Authority
- DE
- Germany
- Prior art keywords
- alkaloids
- china
- salol
- alkali
- dilute
- 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 - Lifetime
Links
- 229930013930 alkaloids Natural products 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N Phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229960000969 phenyl salicylate Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 239000001576 FEMA 2977 Substances 0.000 description 1
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 1
- 229960003110 Quinine Sulfate Drugs 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE Up. CLASS Up.
in FRANKFURT a. M.in FRANKFURT a. M.
Zusatz zum Patente 128116 vom 25. September 1900.Addendum to patent 128116 from September 25, 1900.
Patentirt im Deutschen Reiche vom 5. Dezember igoo ab. Längste Dauer: 24. September 1915.Patented in the German Empire from December 5th igoo. Longest duration: September 24, 1915.
Gemäfs Patent 128116 stellt man Acidylderivate der Chinaalkaloide dadurch her, dafs man auf die Chinaalkaloide die Alphylester organischer Säuren mit Ausnahme der Phenolcarbonate einwirken läfst.Acidyl derivatives are prepared in accordance with patent 128116 of the china alkaloids by adding the alpha esters of organic acids to the china alkaloids, with the exception of the phenol carbonates has an effect.
Es ist nun auch möglich, statt der reinen Alkaloide deren Salze, welche leichter zugänglich sind, zu verwenden.It is now also possible, instead of the pure alkaloids, to use their salts, which are more easily accessible are to be used.
Zu diesem Behufe verfährt man beispielsweise derart, dafs man 36,05 kg wasserfreies oder 39,65 kg wasserhaltiges Chininmonochlorhydrat mit 21,4 kg oder einen Ueberschufs von Salol mehrere Stunden auf 140 bis 1500 erhitzt. Das Reactionsproduct wird mit Benzol zerrieben und die Base der benzolischen Lösung durch eine verdünnte Säure entzögen. Durch Zusatz eines Alkalis wird das Salicyl chinin aus der sauren Lösung gefällt und kann durch Umkrystallisiren aus verdünntem Alkohol gereinigt werden. Die Eigenschaften sind in dem Haupt-Patent bereits beschrieben.For this purpose the procedure is, for example, in such a way, that one 36.05 kg of anhydrous or water-containing 39.65 kg Chininmonochlorhydrat 21.4 kg of an above Schufs salol several hours at 140 to 150 0 heated. The reaction product is triturated with benzene and the base is removed from the benzene solution with a dilute acid. By adding an alkali, the salicylquinine is precipitated from the acidic solution and can be purified by recrystallization from dilute alcohol. The properties are already described in the main patent.
Man kann auch andere Chininsalze verwenden, beispielsweise 20 kg gewöhnliches Chininsulfat mit 50 kg Salol mehrere Stunden auf 140 bis ι 500 erwärmen. Das Reactionsproduct wird in Chloroform gelöst, die Base mit verdünnter Säure ausgeschüttelt und mit Alkali gefällt. Durch Umkrystallisiren aus verdünntem Alkohol wird das Salicylchinin rein erhalten.You can also use other quinine salts, for example 20 kg of common quinine sulfate with 50 kg of Salol for several hours to 140 to ι 50 0 heat. The reaction product is dissolved in chloroform, the base extracted with dilute acid and precipitated with alkali. The salicylquinine is obtained in pure form by recrystallizing from dilute alcohol.
Zur Darstellung von Salicylchinidin werden 20 kg Chinidinchlorhydrat und 40 kg Salol mehrere Stunden auf 140 bis 1500 erhitzt. Das Reactionsproduct wird wie oben behandelt, die durch Alkali abgeschiedene Base löst man in Aether, durch Zusatz von Salicylsäure erhält man das salicylsäure Salicylchinidin, welches aus verdünntem Alkohol in weifsen, bei i68° schmelzenden Nadeln krystallisirt.For the preparation of Salicylchinidin 20 kg and 40 kg Chinidinchlorhydrat salol be heated for several hours at 140 to 150 0th The reaction product is treated as above, the base separated by alkali is dissolved in ether, salicylic acid salicylquinidine is obtained by adding salicylic acid, which crystallizes from dilute alcohol in white needles which melt at 160 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT12014D AT12014B (en) | 1900-12-04 | 1902-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE129452C true DE129452C (en) |
Family
ID=397915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1900129452D Expired - Lifetime DE129452C (en) | 1900-12-04 | 1900-12-04 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE129452C (en) |
-
1900
- 1900-12-04 DE DE1900129452D patent/DE129452C/de not_active Expired - Lifetime
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