DE613066C - Process for the preparation of 8-oxychinaldine - Google Patents
Process for the preparation of 8-oxychinaldineInfo
- Publication number
- DE613066C DE613066C DEI48655D DEI0048655D DE613066C DE 613066 C DE613066 C DE 613066C DE I48655 D DEI48655 D DE I48655D DE I0048655 D DEI0048655 D DE I0048655D DE 613066 C DE613066 C DE 613066C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- oxychinaldine
- preparation
- nitrophenol
- sulfuric acid
- 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
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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 8-Oxychinaldin Es wurde gefunden, daß man 8-Oxychinaldin in sehr guten Ausbeuten erhalten kann, wenn man o-Aminophenol auf Crotonaldehyd in schwefelsaurer oder salzsaurer Lösung und in Gegenwart von o-Nitrophenol als Oxydationsmittel bei erhöhter Temperatur einwirken läßt. Die Umsetzung wird vorteilhaft bei Temperaturen zwischen etwa 95 und i2o° ausgeführt, doch tritt sie auch schon bei etwa 9o° ein und kann auch noch bei i3o bis 1q.0° erfolgen.Process for the preparation of 8-oxychinaldine It has been found that you can get 8-Oxychinaldin in very good yields if you o-aminophenol on crotonaldehyde in sulfuric acid or hydrochloric acid solution and in the presence of Allow o-nitrophenol to act as an oxidizing agent at elevated temperature. The implementation is advantageously carried out at temperatures between about 95 and 120 °, but occurs it already starts at around 9o ° and can also be done at i3o to 1q.0 °.
Gegenüber den bekannten Oxydationsmitteln, wie Nitrobenzolsulfonsäure, bietet die Verwendung von o-Nitrophenol den Vorteil wesentlich besserer Ausbeuten. So erhält man bei Verwendung von Nitrobenzolsulfonsäure als Oxydationsmittel aus 22o Teilen o-Aminophenol in schwefelsaurer Lösung 150 bis i 6o Teile 8-Oxychinaldin, dagegen bei Verwendung von o-Nitrophenol aus der gleichen Menge o-Aminophenol 295 Teile 8-Oxychinaldin, wenn man in schwefelsaurer und 370 bis 38o Teile 8-Oxychinaldin, wenn man in salzsaurer Lösung arbeitet. Beispiel Man trägt 22o Teile o-Aminophenol (etwa 98%ig) und rq,o Teile o-Nitrophenol in 85o Teile 69%ige Schwefelsäure ein, erhitzt das Gemisch auf i i o° und läßt unter gutem Rühren bei einer Temperatur zwischen iio und 115° 2io Teile Crotonaldehyd langsam zufließen. Nach beendetem Zufließen hält man die Temperatur noch eine kurze Zeit lang auf i oo bis i i o°, verdünnt darauf mit Wasser und destilliert das überschüssige o-Nitrophenol mit Wasserdampf ab. Sodann macht man durch Zugabe von Ammoniak oder Alkali kongoneutral, filtriert und versetzt das Filtrat unter Kühlung mit überschüssigem Ammoniak. Das ausgefallene 8-Oxychinaldin wird abgesaugt, mit kaltem Wasser gewaschen und im Vakuum destilliert. Ausbeute: 295 Teile.Compared to the known oxidizing agents, such as nitrobenzenesulfonic acid, the use of o-nitrophenol offers the advantage of significantly better yields. Is obtained when using nitrobenzenesulfonic acid as the oxidizing agent from 22o parts of o-aminophenol in a sulfuric acid solution 1 50 to i 6o parts of 8-Oxychinaldin the other hand, with the use of o-nitrophenol from the same amount of o-aminophenol 295 parts of 8-Oxychinaldin when in sulfuric acid and 370 to 380 parts of 8-oxychinaldine, if one works in hydrochloric acid solution. EXAMPLE 220 parts of o-aminophenol (about 98% strength) and rq.0 parts of o-nitrophenol are introduced into 85o parts of 69% strength sulfuric acid, the mixture is heated to 110 ° and left with thorough stirring at a temperature between 110 and 115 ° Slowly pour in 2io parts of crotonaldehyde. After the inflow has ended, the temperature is kept at 10 to 10 ° for a short time, then diluted with water and the excess o-nitrophenol is distilled off with steam. The mixture is then made Congo neutral by adding ammonia or alkali, filtered and the filtrate is treated with excess ammonia while cooling. The precipitated 8-oxychinaldine is filtered off with suction, washed with cold water and distilled in vacuo. Yield: 295 parts.
Verwendet man an Stelle der Schwefelsäure goo Teile einer 3 i %igen Salzsäure und arbeitet man bei 95 bis io5° unter sonst gleichen Bedingungen wie in Absatz i angegeben, so erhält man 37o bis 38o Teile 8-Oxychinaldin.If you use parts of a 3 i% strength instead of sulfuric acid goo Hydrochloric acid and one works at 95 to 105 ° under otherwise the same conditions as given in paragraph i, 37o to 38o parts of 8-oxychinaldine are obtained.
Das so erhaltene 8-Oxychinaldin ist für technische Zwecke genügend rein. Durch Umlösen aus Methanol, durch Wasserdampfdestillation, durch Zerlegen der mineralsauren Salze mit Alkali oder durch Umkristallisieren der Alkaliverbindungen und Zerlegung dieser mit Säuren kann man das 8-Oxychinaldin in chemisch reiner Form erhalten.The 8-oxyquininaldine thus obtained is sufficient for technical purposes pure. By redissolving from methanol, by steam distillation, by decomposition the mineral acid salts with alkali or by recrystallizing the alkali compounds and decomposition of this with acids one can get the 8-Oxychinaldin in chemically pure form obtain.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48655D DE613066C (en) | 1933-12-24 | 1933-12-24 | Process for the preparation of 8-oxychinaldine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48655D DE613066C (en) | 1933-12-24 | 1933-12-24 | Process for the preparation of 8-oxychinaldine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE613066C true DE613066C (en) | 1935-05-10 |
Family
ID=7192348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48655D Expired DE613066C (en) | 1933-12-24 | 1933-12-24 | Process for the preparation of 8-oxychinaldine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE613066C (en) |
-
1933
- 1933-12-24 DE DEI48655D patent/DE613066C/en not_active Expired
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