CH202247A - Process for the preparation of oxyphenylaminonaphthalene derivatives. - Google Patents
Process for the preparation of oxyphenylaminonaphthalene derivatives.Info
- Publication number
- CH202247A CH202247A CH202247DA CH202247A CH 202247 A CH202247 A CH 202247A CH 202247D A CH202247D A CH 202247DA CH 202247 A CH202247 A CH 202247A
- Authority
- CH
- Switzerland
- Prior art keywords
- derivatives
- preparation
- parts
- oxyphenylaminonaphthalene
- condensation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical class NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkali metal sulfite Chemical class 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-BJUDXGSMSA-N sodium-22 Chemical group [22Na] KEAYESYHFKHZAL-BJUDXGSMSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Ogyphenylaminonaphthalinderivaten. Nachdem im schweizerischen Patent 195324 beschriebenen Verfahren wird bei der Her stellung von Oxyphenylaminonaphthalinderi- vaten durch Kondensation von Oxynaphtha- linen mit Aminooxybenzolen in Gegenwart von Bisulfitlauge eine Verbesserung dadurch bewirkt, dass dem Umsetzungsgemisch neu trales Alkalisulfit zugesetzt wird.
Dieses verbesserte Arbeitsverfahren lässt sich nun auch bei der ebenfalls bekannten Kondensation von Aminonaphthalinen mit Aminooxybenzolen (siehe schweiz. Patent Nr. 132030) anwenden.
Gegenstand des vorliegenden Patentes ist also ein Verfahren zur Herstellung von Oxy- phenylaminonaphthalinderivaten durch Kon densation von Aminonaphthalinen mit Amino- oxybenzolen in Gegenwart von Bisulfitauge, welches dadurch gekennzeichnet ist, dass man ausserdem noch ein neutrales Alkalisulfit zusetzt.
<I>Beispiel 1:</I> In einem verbleiten, geschlossenen Rühr- kessel werden 143 Teile 2-Aminonaphthalin und 138 Teile 4-Amino-l-oxybenzol in einer Lösung von 314 Teilen Natriumbisulfit und 22 Teilen Natriumcarbonat in 1060 Teilen Wasser etwa 5 Stunden bei 160 erhitzt. Das Kondensationsprodukt wird abgesaugt und mit heissem Wasser nachgewaschen. Die Ausbeute beträgt 225-228 Teile 2-(4'-Oxy- phenyl)-aminonaphthalin.
<I>Beispiel 2:</I> 298 Teile 1-Aminonaphthalin und 288 Teile 4-Amino-l-oxybenzol werden zu einer Lösung von 655 Teilen Natriumbisulfit und 45 Teilen Natriumcarbonat in 2200 Teilen Wasser etwa 5 Stunden bei 15011 gerührt. Nach dem Abkühlen wird das Umsetzungs gut abgesaugt, mit Wasser und zum Schluss mit verdünnter Salzsäure nachgewaschen. Auf diese Weise erhält man 1-(4'-Oxyphenyl)- amirionaphthalin mit einem Schmelzpunkt von 80 , nach dem Umkristallisieren von 91 .
Process for the preparation of ogyphenylaminonaphthalene derivatives. After the process described in Swiss patent 195324, an improvement is achieved in the manufacture of oxyphenylaminonaphthalene derivatives by condensation of oxynaphthalene with aminooxybenzenes in the presence of bisulfite liquor by adding neutral alkali metal sulfite to the reaction mixture.
This improved working process can now also be used in the also known condensation of aminonaphthalenes with aminooxybenzenes (see Swiss patent no. 132030).
The present patent therefore relates to a process for the preparation of oxyphenylaminonaphthalene derivatives by condensation of aminonaphthalenes with aminoxybenzenes in the presence of bisulfite solution, which is characterized in that a neutral alkali metal sulfite is also added.
Example 1: In a leaded, closed stirred kettle, about 143 parts of 2-aminonaphthalene and 138 parts of 4-amino-1-oxybenzene are dissolved in a solution of 314 parts of sodium bisulfite and 22 parts of sodium carbonate in 1060 parts of water Heated at 160 for 5 hours. The condensation product is filtered off and washed with hot water. The yield is 225-228 parts of 2- (4'-oxyphenyl) aminonaphthalene.
Example 2: 298 parts of 1-aminonaphthalene and 288 parts of 4-amino-1-oxybenzene are stirred at 15011 for about 5 hours to a solution of 655 parts of sodium bisulfite and 45 parts of sodium carbonate in 2200 parts of water. After cooling, the reaction is well suctioned off, washed with water and finally with dilute hydrochloric acid. In this way, 1- (4'-oxyphenyl) - amirionaphthalene with a melting point of 80 is obtained, and 91 after recrystallization.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE202247X | 1935-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH202247A true CH202247A (en) | 1939-01-15 |
Family
ID=5770548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH202247D CH202247A (en) | 1935-10-26 | 1936-05-22 | Process for the preparation of oxyphenylaminonaphthalene derivatives. |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH202247A (en) |
| NL (1) | NL43412C (en) |
-
0
- NL NL43412D patent/NL43412C/xx active
-
1936
- 1936-05-22 CH CH202247D patent/CH202247A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL43412C (en) |
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