CH205786A - Process for the preparation of 7-methyl-2-amino-3-methoxy-diphenylene oxide. - Google Patents
Process for the preparation of 7-methyl-2-amino-3-methoxy-diphenylene oxide.Info
- Publication number
- CH205786A CH205786A CH205786DA CH205786A CH 205786 A CH205786 A CH 205786A CH 205786D A CH205786D A CH 205786DA CH 205786 A CH205786 A CH 205786A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- methoxy
- diphenylene oxide
- amino
- preparation
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 7-Nethyl-2-amino-3-methogy-diphenylenogyd. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung von 7-Methyl-2-amino-3-methoxy-diphenylenoxyd, welches dadurch gekennzeichnet ist, dass man 7-Methyl-3-inethoxy-diphenylenoxyd nitriert und das erhaltene 7-Methyl-2-nitro-3-methoxy- diphenylenoxyd reduziert.
Die erhaltene Verbindung stellt ein wert volles Zwischenprodukt zur Herstellung von Farbstoffen dar.
Beispiel: 28 Gewichtsteile 7-Methyl-3-oxydipheny- lenoxyd, das durch Schmelzen von 4'-Methyl- 2'-chlor-2,5-dioxydiphenyl vom F. 148 C mit Ätzkali leicht erhältlich ist, werden mit 30 Gewichtsteilen Wasser und 35 Gewichtsteilen Natronlauge 40 Bö auf dem Dampfbade ge rührt und zu der Schmelze am Rückfluss 26 Gewichtsteile Dimethylsulfat zugetropft. Man heizt eine Stunde nach und verdünnt dann mit kaltem Wasser.
Der abgeschiedene Me- thyläther wird abgesaugt und gründlich aus- gewaschen. Das 7-Methyl-3-methoxy-dipheny- lenoxyd siedet im Vakuum bei 3 mm bei 138 bis<B>1390</B> C und schmilzt aus Methanol umkristallisiert bei 49 bis 51 C.
50 Gewichtsteile 7-Methyl-3-metboxy- diphenylenoxyd werden mit 250 Gewichts teilen Chlorbenzol und 50 Gewichtsteilen Salpetersäure vom spezifischen Gewicht 1,4 verrührt. Die Temperatur des Reaktions gemisches steigt auf etwa<B>500</B> C, die Reak tion ist dann beendet. Nach dem Erkalten wird das abgeschiedene 7-Methyl-2-nitro-3- methoxy-diphenylenoxyd abgesaugt und mit Wasser neutral gewaschen. Man erhält un mittelbar 50 Gewichtsteile reine Nitrover- bindung vom F. 170 bis<B>171'</B> C. Die Nitro- verbindung wird in üblicher Weise kataly tisch oder mit Eisen und Säuren reduziert.
Das so erhaltene, bisher nicht bekannte 7-Methyl- 2-amino- 3-methoxy-diphenylenoxyd kristallisiert aus Methanol in farblosen Kri stallen vom F.<B>117</B> bis 118<B>0</B> C. Es bildet ein schwer lösliches farbloses Chlorhydrat und lässt sich leicht diazotieren.
Process for the preparation of 7-Nethyl-2-amino-3-methogy-diphenylenogyd. The subject of the present additional patent is a process for the production of 7-methyl-2-amino-3-methoxy-diphenylene oxide, which is characterized in that 7-methyl-3-ynethoxy-diphenylene oxide is nitrated and the 7-methyl-2 obtained -nitro-3-methoxy-diphenylene oxide reduced.
The compound obtained is a valuable intermediate for the production of dyes.
Example: 28 parts by weight of 7-methyl-3-oxydiphenylene oxide, which can easily be obtained by melting 4'-methyl-2'-chloro-2,5-dioxydiphenyl with a temperature of 148 ° C. with caustic potash, are mixed with 30 parts by weight of water and 35 parts by weight of sodium hydroxide solution 40 Boo ge on the steam bath and added dropwise to the melt at reflux 26 parts by weight of dimethyl sulfate. The mixture is heated for an hour and then diluted with cold water.
The separated methyl ether is suctioned off and thoroughly washed out. The 7-methyl-3-methoxy-diphenylene oxide boils in vacuo at 3 mm at 138 to 1390 C and melts recrystallized from methanol at 49 to 51 C.
50 parts by weight of 7-methyl-3-metboxy-diphenylene oxide are mixed with 250 parts by weight of chlorobenzene and 50 parts by weight of nitric acid with a specific gravity of 1.4. The temperature of the reaction mixture rises to about <B> 500 </B> C, and the reaction is then complete. After cooling, the separated 7-methyl-2-nitro-3-methoxy-diphenylene oxide is filtered off with suction and washed neutral with water. 50 parts by weight of pure nitro compound with a melting point of 170 to 171 ° C. are obtained directly. The nitro compound is reduced in the usual way catalytically or with iron and acids.
The previously unknown 7-methyl-2-amino-3-methoxy-diphenylene oxide obtained in this way crystallizes from methanol in colorless crystals from F. <B> 117 </B> to 118 <B> 0 </B> C. It forms a poorly soluble, colorless hydrochloride and can be easily diazotized.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE205786X | 1936-02-19 | ||
CH199184T | 1937-02-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH205786A true CH205786A (en) | 1939-06-30 |
Family
ID=25723211
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH205786D CH205786A (en) | 1936-02-19 | 1937-02-12 | Process for the preparation of 7-methyl-2-amino-3-methoxy-diphenylene oxide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH205786A (en) |
-
1937
- 1937-02-12 CH CH205786D patent/CH205786A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH205786A (en) | Process for the preparation of 7-methyl-2-amino-3-methoxy-diphenylene oxide. | |
CH205788A (en) | Process for the preparation of 2-amino-3,7-dimethoxy-diphenylene oxide. | |
CH205789A (en) | Process for the preparation of 6-methyl-2-amino-3-methoxy-diphenylene oxide. | |
CH205787A (en) | Process for the preparation of 7-chloro-2-amino-3-methoxy-diphenylene oxide. | |
CH205785A (en) | Process for the preparation of 2-amino-3-ethoxy-diphenylene oxide. | |
DE681640C (en) | Process for the preparation of 2-amino-3-alkoxydiphenylene oxides and their substitution products | |
AT129783B (en) | Process for the preparation of 2-oxymethylbenzimidazolaric acids. | |
CH257944A (en) | Process for the production of a vat dye. | |
AT152830B (en) | Process for the preparation of compounds from dialkyl and alkylaryl barbituric acids and urea derivatives. | |
DE444325C (en) | Process for the preparation of a naphthalene sulfocarboxylic acid anhydride | |
AT64974B (en) | Process for the preparation of N-haloalkyl-CC-dialkylbarbituric acids. | |
DE609025C (en) | Process for the preparation of condensation products of the arylene thiazole series | |
AT88673B (en) | Process for the preparation of haloethylmorphines. | |
AT121731B (en) | Process for the preparation of monooxy-ω-alkylaminoacetophenones. | |
CH205774A (en) | Process for the preparation of 7-chloro-3-oxydiphenylene oxide. | |
CH205783A (en) | Process for the preparation of 8-methyl-3-oxy-diphenylene oxide. | |
CH124934A (en) | Process for the preparation of 6-methoxy-N-ethyl-a-diethylamino-d-methyl-butyl-8-aminoquinoline. | |
CH212589A (en) | Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. | |
CH205773A (en) | Process for the preparation of 7-methyl-3-oxydiphenylene oxide. | |
CH136553A (en) | Process for the preparation of a descendant of the pyrazolanthrone. | |
CH314845A (en) | Process for the preparation of guanylhydrazono-pyruvaldehyde-m-guanyl-phenylhydrazone-carbonate | |
CH205779A (en) | Process for the production of 3,6-dioxy-diphenylene oxide. | |
CH214333A (en) | Process for the preparation of 5- (N-ethylcarbazolyl-3'-amino) -2-butoxy-3.6-dichloro-1.4-benzoquinone. | |
CH220928A (en) | Process for the preparation of a reactive chlorine-containing isatin compound. | |
CH188882A (en) | Process for the preparation of a 2-oxychrysenic monosulfonic acid. |