AT50287B - Process for the preparation of quinine diglycolate. - Google Patents
Process for the preparation of quinine diglycolate.Info
- Publication number
- AT50287B AT50287B AT50287DA AT50287B AT 50287 B AT50287 B AT 50287B AT 50287D A AT50287D A AT 50287DA AT 50287 B AT50287 B AT 50287B
- Authority
- AT
- Austria
- Prior art keywords
- quinine
- preparation
- diglycolate
- parts
- diglycolic acid
- Prior art date
Links
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound 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 title claims description 12
- 235000001258 Cinchona calisaya Nutrition 0.000 title claims description 6
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 title claims description 6
- 229960000948 quinine Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims 3
- QEVGZEDELICMKH-UHFFFAOYSA-L 2-(carboxylatomethoxy)acetate Chemical compound [O-]C(=O)COCC([O-])=O QEVGZEDELICMKH-UHFFFAOYSA-L 0.000 title description 2
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical group CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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form gelöst und durch Ausschütteln mit kleinen Mengen verdünnter Essigsäure von unverändertem Chinin befreit. Darauf wird die Chloroformlösung getrocknet und eingedampft. Es hinterbleibt derDiglykolsäurechininester.
Beispiel IV : 0'6 Teile Magnesium werden nach Grignard in Äther mit 3 Teilen Äthylbromid umgesetzt und unter gutem Rühren und Kühlen 8 Teile in Chloroform gelöstes Chinin in die ätherische Flüssigkeit eingetragen. Nach beendetem Eintragen wird schwach erwärmt. Nach erneuter Abkühlung fügt man 3 Teile Diglykolsäurechlorid hinzu, erwärmt schwach und kocht schliesslich 1 Stunde. Den organischen Lösungsmitteln wird das überschüssige Chinin durch Ausschütteln mit kleinen Mengen 1 prozentiger Schwefelsäure entzogen, darauf di Ätherchloroform-
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form and freed from unchanged quinine by shaking with small amounts of dilute acetic acid. The chloroform solution is then dried and evaporated. The quinine diglycolate remains behind.
Example IV: According to Grignard, 0'6 parts of magnesium are reacted in ether with 3 parts of ethyl bromide, and 8 parts of quinine dissolved in chloroform are added to the ethereal liquid with thorough stirring and cooling. After the end of the entry is slightly warmed. After cooling again, 3 parts of diglycolic acid chloride are added, the mixture is warmed gently and finally boiled for 1 hour. The excess quinine is removed from the organic solvents by shaking out small amounts of 1 percent sulfuric acid, then the ether chloroform
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Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT50287T | 1910-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT50287B true AT50287B (en) | 1911-10-25 |
Family
ID=3571124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT50287D AT50287B (en) | 1910-06-27 | 1910-06-27 | Process for the preparation of quinine diglycolate. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT50287B (en) |
-
1910
- 1910-06-27 AT AT50287D patent/AT50287B/en active
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