DE497908C - Process for the preparation of nitrogen-containing anthraquinone derivatives - Google Patents
Process for the preparation of nitrogen-containing anthraquinone derivativesInfo
- Publication number
- DE497908C DE497908C DEI27618D DEI0027618D DE497908C DE 497908 C DE497908 C DE 497908C DE I27618 D DEI27618 D DE I27618D DE I0027618 D DEI0027618 D DE I0027618D DE 497908 C DE497908 C DE 497908C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- anthraquinone derivatives
- nitrogen
- nitro
- anthraquinone
- 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
- -1 nitrogen containing anthraquinone derivatives Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N Isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 210000004940 Nucleus Anatomy 0.000 description 1
- QCMGYKJTPOJMAH-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=2C(C3=CC=C(C(=C3C(C1=2)=O)[N+](=O)[O-])C)=O)C Chemical compound [N+](=O)([O-])C1=C(C=CC=2C(C3=CC=C(C(=C3C(C1=2)=O)[N+](=O)[O-])C)=O)C QCMGYKJTPOJMAH-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Description
Verfahren zur Darstellung von stickstoffbaltigen Anthrachinonderivaten Aus der Patentschrift 3 6o 42 2 ist ein Verfahren zur Darstellun von stickstoffhaltigen 9 g Anthrachinanderivate,a bekannt geworden, das darin besteht, daß man rauchende Schwefelsäure auf i-Nitro-2-alk-ylanthracl-änone oder deren Kernsubstitutionsprodukte einwirken läßt.Method for the preparation of nitrogen-containing anthraquinone derivatives From the patent specification 3 6o 42 2 a method for the preparation of nitrogen-containing 9 g anthraquinone derivatives, a has become known, which consists in that fuming sulfuric acid on i-nitro-2-alk-ylanthracl-änones or their Allow nuclear substitution products to act.
Es ist nun weiter gefunden worden, daß sich. diese Reaktion auch auf solche Anthrachinonderivate anwenden läßt, welche die a--Nitro-ß-al-kylgruppierung in o-Stellun- zueinander mehrmals im Molekül enthalten. So entstehen z. B. auf diese 'Weise aus den entsprechenden Dinitredimethylanthrachinonen unter Austritt von 2 Moleküle Wasser neue Verbindungen-, wahrscheinlich Anthrachi#nondüsoxazole, die als Zwischenprodukte für die Gewinnung von Farbstoffen wertvoll sind.It has now been further found that. this reaction too can use such anthraquinone derivatives, which the a - nitro-ß-alkyl group contained several times in the molecule in the o-position to one another. So arise z. B. on this 'From the corresponding dinitredimethylanthraquinones with the escape of 2 Molecules of water new compounds-, probably anthrachi # nondüsoxazole, the are valuable as intermediate products for the production of dyes.
Bei derEinwirkung v(Yxi rauchender Schwefelsäure auf Dinitroanthrachinone bilden sich bekanntlich im allgemeinen Nitromitrosooxyanthrachinone, indem zunächst ein Sauerstoff aus nur einer Nitrogruppe in den Kern verschoben wird (vgl. die Patentschrift io4 282, Kl. 22). Der Bildung der Isoxazole geht wohl eine ähnliche Wanderung von Nitrosauerstoff, hier aber in die o-ständige Seite-nkette unter Zwischenbildung von Nitrosoalkoholen' voraus. So entsteht nach der Patentschrift 36o 422, Beispiel 2, aus 1, 5-DinitrO-2-methyl-' anthrachinon besonders leicht ein 5-Nitro- 1-, 2-anthrachinonisoxazol: wobei also in normaler Weise nur eine L\Iitrogruppe umgewandelt wird und die zweite als solche erhalten bleibt. Es bildet sich nicht etwa unter Beteiligung beider Nitrogruppen ein iNitrosooxyanthrachinonisoxazol. Daher war es überraschend und keineswegs vorauszusehen, daß beide Nitrogiuppen eines Dinitroanthrachinons so leicht durch rauchende Schwefelsäure eine Umlag gerung erfahren würden, sobald zu jeder in o-Stellung sich eine Alk-ylgruppe befindet, z. B.: Beispiele i. io Gewichtsteile il, 5-Dini-troc#2, 6-dimethyr.-anthrachinon (vom Zersetzungspunkt über 35o', erhalten durch Nitrierung von 2,6-3)#imetliylanthrachinon vom Schmelzpunkt 239 bis 240' mit Salpeterschwefelsäure) werden unter raschem Rühren und guter Kühlung in ioo Gewichtsteile rauchende Schwefelsäure von 65 O/o Anhydrid-gehalt eingetragen. -Nach kurzem Nachrühren wird auf Eis ausgegossen, wobei sich- das Reaktionspro,dulkt, vermutlich Anthrachinon-1,2,5,6-düsoxazol, in braun-,-elben Flocken ausscheidet. In trockenem Zustande stellt es einbraungelbes Pulver dar, das in kalten Alkalien unlöslich ist. Die Farbe der Lösung in konzentrierter Schwefelsäure ist braungelb, zi 2. In gleicher Weise,erhält man, ausgehend von 1, 8 - Dinitro - 2, 7 - dimethylanthrachinon (vom Schmelzpunkt 298 bis 299' unter Zersetzulig, gewonnen durch Nitrierung, von 2,7-'Dimethylantbrachinon vom Schmelzpunkt 169'), ein olivbraunes Reaktionsprodukt,. das das Anthrachinon-I.2.8.7-,diisoxazol darstellen dürfte und dem Isomeren des Beispiels i ähnlich ist.When fuming sulfuric acid acts on dinitroanthraquinones, as is well known, nitromitrosooxyanthraquinones are generally formed by initially displacing an oxygen from only one nitro group into the nucleus (cf. patent specification IO4,282 , cl. 22). The formation of isoxazoles is probably similar migration of nitro oxygen, but here permanent o-in the side-nkette interposition formation of Nitrosoalkoholen 'ahead. the result according to the patent 36o 422, example 2, 1, 5-dinitro-2-methyl-' anthraquinone particularly easy a 5- Nitro-1-, 2-anthraquinone isoxazole: where normally only one nitro group is converted and the second is retained as such. An i-nitrosooxyanthraquinone isoxazole is not formed with the participation of both nitro groups. It was therefore surprising and by no means to be foreseen that both nitro groups of a dinitroanthraquinone would so easily undergo rearrangement by fuming sulfuric acid as soon as there is an alk-yl group to each in the o-position, e.g. B .: Examples i. 10 parts by weight of 5-dinotroc # 2, 6-dimethyr.-anthraquinone (from the decomposition point above 35o ', obtained by nitration of 2.6-3) #imetliylanthraquinone from melting point 239 to 240' with nitric sulfuric acid) are stirred rapidly and good cooling in 100 parts by weight of fuming sulfuric acid with an anhydride content of 65%. After a short further stirring, it is poured onto ice, with the reaction product, presumably anthraquinone-1,2,5,6-düsoxazole, precipitating in brown -, - yellow flakes. When dry it is a brownish-yellow powder, which is insoluble in cold alkalis. The solution color in concentrated sulfuric acid is brown yellow, zi 2. In the same way, is obtained, starting from 1, 8 - dinitro - 2, 7 - dimethylanthraquinone (of melting point 298-299 'under Zersetzulig obtained by nitration of 2, 7-'Dimethylantbrachinon with a melting point of 169'), an olive-brown reaction product. which should represent the anthraquinone-I.2.8.7-, diisoxazole and is similar to the isomer of Example i.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI27618D DE497908C (en) | 1926-03-09 | 1926-03-09 | Process for the preparation of nitrogen-containing anthraquinone derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI27618D DE497908C (en) | 1926-03-09 | 1926-03-09 | Process for the preparation of nitrogen-containing anthraquinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE497908C true DE497908C (en) | 1930-05-16 |
Family
ID=7186811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI27618D Expired DE497908C (en) | 1926-03-09 | 1926-03-09 | Process for the preparation of nitrogen-containing anthraquinone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE497908C (en) |
-
1926
- 1926-03-09 DE DEI27618D patent/DE497908C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2025662A1 (en) | ||
| DE2142100B2 (en) | PROCESS FOR SEPARATING ANTHRACHINON NITRATION PRODUCTS FROM THE LIQUID | |
| DE497908C (en) | Process for the preparation of nitrogen-containing anthraquinone derivatives | |
| DE564788C (en) | Process for the preparation of derivatives of I, I'-dianthraquinonyl | |
| DE722554C (en) | Process for the production of methyl pentaerythritol trinitrate | |
| DE511451C (en) | Process for the preparation of 3- or 5-iodine substitution products of pyridine | |
| DE527618C (en) | Process for the production of heavy metal salts from sulphonic acids | |
| DE347819C (en) | Process for the production of 3íñ6 - diaminoacridine | |
| DE415318C (en) | Process for the preparation of 4-arylamino-1-arylimino-2-naphthoquinones | |
| DE468453C (en) | Process for the preparation of dinitroperylene and its derivatives | |
| DE318948C (en) | Process for the preparation of water-soluble condensation products | |
| DE462352C (en) | Process for the preparation of isoxazines of the anthraquinone series | |
| DE890403C (en) | Process for the production of mordant dyes | |
| DE555410C (en) | Process for the preparation of 4-oxy-5-nitroisophthalic acid | |
| AT114219B (en) | Process for the preparation of dinitroperylenes and dinitroperylenes of haloperylenes. | |
| DE540247C (en) | Process for the production of water-soluble products from wool fat | |
| DE515111C (en) | Process for the preparation of 3-nitro-5-ketotetrahydronaphthalene | |
| DE240521C (en) | ||
| DE72173C (en) | Process for the preparation of nitrated bases from benzylidene compounds of primary aromatic monamines | |
| DE901056C (en) | Process for the isolation of amino acids | |
| DE1025411B (en) | Process for the preparation of 1-chloro-2, 4, 6-trinitrobenzene by nitration of 1-chloro-2, 4-dinitrobenzene | |
| DE536080C (en) | Process for making antiseptic agents | |
| DE119756C (en) | ||
| DE271745C (en) | ||
| DE466440C (en) | Process for the representation of tanning substances |