CH188510A - Process for the preparation of 1-isobutyl-3-oxytetrahydroquinoline. - Google Patents
Process for the preparation of 1-isobutyl-3-oxytetrahydroquinoline.Info
- Publication number
- CH188510A CH188510A CH188510DA CH188510A CH 188510 A CH188510 A CH 188510A CH 188510D A CH188510D A CH 188510DA CH 188510 A CH188510 A CH 188510A
- Authority
- CH
- Switzerland
- Prior art keywords
- isobutyl
- oxytetrahydroquinoline
- preparation
- free base
- epichlorohydrin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- GGARKJIWYNVMBF-UHFFFAOYSA-N n-(2-methylpropyl)aniline Chemical compound CC(C)CNC1=CC=CC=C1 GGARKJIWYNVMBF-UHFFFAOYSA-N 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Description
Verfahren zur Darstellung von 1-Isobutyl-3-oaytetrahydrochinolin. Gemäss dem im Hauptpatent beschriebe nen Verfahren erhält man 1-Butyl-3-oxy- tetrahydrochinolin, wenn man n-Butylanilin mit Epichlorhydrin bei Temperaturen über <B>130'</B> C behandelt und aus dem Reaktions produkt die freie Base durch Alkalizusatz abtrennt.
Wie nun weiter gefunden wurde, kann man in ganz analoger Weise auch das bisher nicht bekannte 1-Isobutyl-3-oxytetrahydro- chinolin erhalten, wenn man Isobutylanilin mit Epichlorhydrin bei Temperaturen über 130 C behandelt und aus dem Reaktions produkt die freie Base durch Alkalizusatz abtrennt.
Das Endprodukt dient als Zwischenpro dukt für die Herstellung von Farbstoffen. Beispiel: 179 Teile Isobutylanilin werden mit 337 Teilen Epichlorhydrin 6 ,Stunden auf 130 bis 140' erhitzt. Darauf lässt man abkühlen, setzt verdünnte Natronlauge dazu und erhitzt das Gemisch durch Einleiten von Wasser dampf.
Nach dem Erkalten wird das 01 ausgeäthert und im Vakuum destilliert. Man erhält das 1-Isobutyl-3-oxytetrahydrochinolin vom gp,1 <B>157'.</B>
Process for the preparation of 1-isobutyl-3-oaytetrahydroquinoline. According to the process described in the main patent, 1-butyl-3-oxy-tetrahydroquinoline is obtained when n-butylaniline is treated with epichlorohydrin at temperatures above 130 ° C. and the free base is obtained from the reaction product by adding alkali separates.
As has now also been found, the previously unknown 1-isobutyl-3-oxytetrahydroquinoline can also be obtained in a very analogous manner if isobutylaniline is treated with epichlorohydrin at temperatures above 130 ° C. and the free base is separated off from the reaction product by adding alkali .
The end product serves as an intermediate product for the manufacture of dyes. Example: 179 parts of isobutylaniline are heated with 337 parts of epichlorohydrin for 6 hours to 130 to 140 minutes. It is then allowed to cool, dilute sodium hydroxide solution is added and the mixture is heated by passing in steam.
After cooling, the oil is extracted with ether and distilled in vacuo. The 1-isobutyl-3-oxytetrahydroquinoline of gp, 1 157 '. Is obtained
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE188510X | 1934-05-16 | ||
| CH182046T | 1936-02-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH188510A true CH188510A (en) | 1936-12-31 |
Family
ID=25720645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH188510D CH188510A (en) | 1934-05-16 | 1935-01-30 | Process for the preparation of 1-isobutyl-3-oxytetrahydroquinoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH188510A (en) |
-
1935
- 1935-01-30 CH CH188510D patent/CH188510A/en unknown
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