DE85198C - - Google Patents
Info
- Publication number
- DE85198C DE85198C DENDAT85198D DE85198DA DE85198C DE 85198 C DE85198 C DE 85198C DE NDAT85198 D DENDAT85198 D DE NDAT85198D DE 85198D A DE85198D A DE 85198DA DE 85198 C DE85198 C DE 85198C
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- nitrobenzaldehyde
- sulfuric acid
- derivatives
- aldehydohydroxylamines
- 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.)
- Active
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000001603 reducing Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 claims description 3
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- GEZMQGHOIAKYSL-UHFFFAOYSA-N 3-nitrosobenzaldehyde Chemical compound O=CC1=CC=CC(N=O)=C1 GEZMQGHOIAKYSL-UHFFFAOYSA-N 0.000 description 1
- JITMZUMTIBUTHH-UHFFFAOYSA-N 4-nitrosobenzaldehyde Chemical compound O=CC1=CC=C(N=O)C=C1 JITMZUMTIBUTHH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- -1 aromatic nitro compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In dem Patente Nr. 75260 und dessen Zusätzen wurde dargethan, dafs bei der elektrolytischen Reduction von aromatischen Nitroverbindungen in concentrirter oder wenig verdünnter Schwefelsäure Amidophenole bezw. deren Derivate entstehen.In the patent No. 75260 and its amendments it was shown that in the case of electrolytic Reduction of aromatic nitro compounds in concentrated or slightly diluted form Sulfuric acid amidophenols respectively. their derivatives arise.
Es wurde nun gefunden, dafs bei der Anwendung von aromatischen Nitroaldehyden unter den gleichen Bedingungen nicht die erwarteten Aldehydoamidophenole, sondern Aldehydohydroxylamine bezw. Derivate (Condensationsproducte) von diesen resultiren. Im Nachfolgenden seien zwei typische Beispiele gegeben.It has now been found that when using aromatic nitroaldehydes under the same conditions not the expected aldehydoamidophenols, but aldehydohydroxylamines respectively Derivatives (condensation products) result from these. Two typical examples are given below.
10 kg m-Nitrobenzaldehyd werden in 150 kg Schwefelsäure gelöst und in der im Patente Nr. 75260 und dessen Zusätzen mehrfach beschriebenen Weise (Spannung des Stromes 4 bis 6 Volt, Stromstärke 1 Ampere, Dichtigkeit an der negativen Elektrode 6 bis 7 Ampere pro qdm, bei gewöhnlicher Temperatur) so lange der elektrolytischen Reduction unterworfen, bis in einer Probe kein unveränderter Nitroaldehyd mehr nachzuweisen ist. Beim Verdünnen mit dem mehrfachen Volumen Wasser scheidet ,sich ein .farbloser, in Wasser unlöslicher Niederschlag ab, welcher ein Anhydroderivat des m- Aldehydophenylhydroxylamins10 kg of m-nitrobenzaldehyde are used in 150 kg Dissolved sulfuric acid and described several times in patent no. 75260 and its additives Way (voltage of the current 4 to 6 volts, current strength 1 ampere, tightness at the negative electrode 6 to 7 amperes per square meter, at normal temperature) so Subjected to electrolytic reduction for a long time, until none of the samples remained unchanged Nitroaldehyde is more to be detected. When diluting with several times the volume of water separates, becomes more colorless, less soluble in water Precipitate, which is an anhydro derivative of m-aldehydophenylhydroxylamine
C1-H/. -.j rr /r\ ττ\ ist. Dasselbe ist identisch D /■ W ti (U JrIJ C 1 -H /. -.j rr / r \ ττ \ is. The same is identical to D / ■ W ti (U JrIJ
mit dem von Bamberger (Ber. d, d. ehem.with that of Bamberger (Ber. d, d.
Ges. 28, 250) bei der Reduction des m-Nitrobenzaldehyds mit Zinkstaub erhaltenen Körper. Es löst sich wie dieser in den üblichen organischen Solventien nicht auf und liefert bei der Oxydation mit Eisenchlorid den von Bamberger am angegebenen Orte beschriebenen m-Nitrosobenzaldehyd vom Schmelzpunkt io6°.Ges. 28, 250) bodies obtained in the reduction of m-nitrobenzaldehyde with zinc dust. Like this one, it does not dissolve in the usual organic solvents and delivers in the Oxidation with ferric chloride as described by Bamberger at the place indicated m-nitrosobenzaldehyde with a melting point of 10 °.
p-Nitrobenzaldehyd in dem gleichen Mengeverhältnifs in concentrirter Schwefelsäure gelöst, liefert unter den in Beispiel 1. beschriebenen Bedingungen ein Reductionsproduct, welches sich durch Zusatz von Wasser als orangegelber, in Wasser, Alkohol, Aether, Schwefelkohlenstoff unlöslicher Niederschlag abscheidet. Aus Nitrobenzol krystallisirt dasselbe in Form breiter orangegelber Nadeln, welche bei ca. 225 ° schmelzen. Der Körper reducirt Fehling'sche Lösung, ist nicht wie der vorige ein Anhydroderivat, sondern hat die Zusammensetzung eines Aldehydophenylhydroxylamins. Bei der Destillation mit wässerigem Eisenchlorid entsteht daraus in glatter Reaction p-Nitrosobenzaldehyd, welcher aus verdünntem Alkohol, in dem er mit grüner Farbe löslich ist, in Form gelblicher Blättchen vom Schmelzpunkt 1360 krystallisirt.Dissolved p-nitrobenzaldehyde in the same proportion in concentrated sulfuric acid yields a reduction product under the conditions described in Example 1, which is deposited as an orange-yellow precipitate which is insoluble in water, alcohol, ether and carbon disulfide when water is added. It crystallizes from nitrobenzene in the form of broad orange-yellow needles, which melt at about 225 °. The body reduces Fehling's solution, is not an anhydrous derivative like the previous one, but has the composition of an aldehydophenylhydroxylamine. In the distillation with aqueous ferric chloride therefrom is formed in a smooth reaction, p-Nitrosobenzaldehyd which from dilute alcohol in which it is soluble with green color, crystallizes in the form of yellowish flakes of melting point 136 0th
Analog verhalten sich andere Nitroaldehyde der aromatischen Reihe.Other nitroaldehydes of the aromatic series behave analogously.
Die Aldehydohydroxylamine bezw. deren Derivate sollen zur Darstellung von FarbstoffenThe aldehydohydroxylamines respectively. their derivatives are intended to represent dyes
oder pharmaceutischen Producten Verwendung finden.or pharmaceutical products are used.
Claims (1)
Die Ausführung des durch Anspruch ι geschützten Verfahrens unter Verwendung von m- oder p-Nitrobenzaldehyd.ι. Process for the preparation of aromatic aldehydohydroxylamines BEzw. of derivatives thereof, consisting in that. aromatic nitroaldehydes, dissolved in concentrated or slightly dilute sulfuric acid, are subjected to the reducing action of the electric current.
The execution of the process protected by claim ι using m- or p-nitrobenzaldehyde.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE85198C true DE85198C (en) |
Family
ID=357360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT85198D Active DE85198C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE85198C (en) |
-
0
- DE DENDAT85198D patent/DE85198C/de active Active
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