CH133473A - Process for the preparation of a descendant of the pyrazolanthrone. - Google Patents
Process for the preparation of a descendant of the pyrazolanthrone.Info
- Publication number
- CH133473A CH133473A CH133473DA CH133473A CH 133473 A CH133473 A CH 133473A CH 133473D A CH133473D A CH 133473DA CH 133473 A CH133473 A CH 133473A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrazolanthrone
- preparation
- bromobenzene
- potash
- copper
- Prior art date
Links
- ACPOUJIDANTYHO-UHFFFAOYSA-N anthra[1,9-cd]pyrazol-6(2H)-one Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=NNC2=C1 ACPOUJIDANTYHO-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229940072033 potash Drugs 0.000 claims description 4
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- NMFBXBSNLQNQKL-UHFFFAOYSA-N 1-chloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=CC=C3C(=O)C2=C1 NMFBXBSNLQNQKL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- -1 phenylpyrazole anthrone Chemical compound 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/04—Pyrazolanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Abkömmlings des Pyrazolanthrons. Es ist gefunden worden, dass neue Ab kömmlinge des Pyrazolanthrons entstehen, wenn man Pyrazolanthron oder ein Pyrazol- anthron, in dem das Wasserstoffatom der NH-Gruppe durch irgend ein Metall ersetzt ist, oder die Derivate oder Substitutionspro- dukte dieser Verbindungen in geeigneter Weise mit Halogensubstitutionsprodukten der aromatischen Reihen, wie der Benzol-,
Naph- talin- oder Anthrachinonreihe umsetzt. Ge nannt seien beispielsweise Halogenbenzole, Nitrohalogenbenzole oder -naphtaline, o-Ha- logencarbonsäuren der Benzol-, Naphtalin- oder Anthrachinonreihe, 1-Chlor-2-methyl- anthrachinon, Halogenbenzanthrone und an dere.
Die Durchführung der Reaktion ge schieht zweckmässig in einem organischen Lösungsmittel unter Zusatz der bekannten, die Abspaltung von Halogenwasserstoffsäure befördernden Katalysatoren, wie Kupferpul ver, Kupfer- und Vanadinsalze usw. und unter Zusatz eines Halogenwasserstoffsäure- bindenden Mittels. In gewissen Fällen ist die Anwendung von Druck notwendig. Die neuen Stoffe sind für die Darstellung von Farb stoffen wertvoll.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des Py-1- Phenylpyrazolanthrons der Formel
EMI0001.0031
durch Aufeinanderwirkenlassen von Brom benzol, Pyrazolanthron und Pottasche in Gegenwart einer geringen Menge eines Kup- ferkatalysators für die Bromwasserstoffab- spaltung.
<I>Beispiel:</I> Gleiche Gewichtsteile Pyrazolanthr-on, Brombenzol und Kaliumcarbonat werden in Gegenwart von etwas Kupfersalz in der zehnfachen Gewichtsmenge Nitrobenzol wäh rend 10 Stunden unter Rühren am Rückfuss zum Kochen erhitzt. Nach dem Erkalten wird mit Sprit verdünnt, filtriert und mit Sprit und Wasser gewaschen und getrocknet. Aus Eisessig kristallisiert das entstandene Phenylpyrazolanthron in schönen grossen gel ben Kristallnadeln, die bei 211-212 schmel zen. Es soll zur Herstellung von Farbstoffen Verwendung finden. Konzentrierte Schwefel säure löst mit roter Farbe ohne Fluoreszenz, organische Lösungsmittel mit mehr oder weniger starker gelber Fluoreszenz.
Das gleiche Produkt entsteht, wenn zu nächst Pyrazolanthron und Pottasche in Ni- trobenzol erhitzt werden bis zur Bildung des roten Kalisalzes des Pyrazolanthrones und dann nach Zugabe von Brombenzol und Kupfer weiter verfahren wird, wie oben be schrieben.
Process for the preparation of a descendant of the pyrazolanthrone. It has been found that new derivatives of the pyrazole anthrone arise when pyrazole anthrone or a pyrazole anthrone in which the hydrogen atom of the NH group has been replaced by any metal, or the derivatives or substitution products of these compounds in a suitable manner Halogen substitution products of the aromatic series, such as benzene,
Naphthalene or anthraquinone series converts. Examples which may be mentioned are halobenzenes, nitrohalobenzenes or naphthalines, o-halocarboxylic acids of the benzene, naphthalene or anthraquinone series, 1-chloro-2-methyl-anthraquinone, halobenzanthrones and others.
The reaction is conveniently carried out in an organic solvent with the addition of the known catalysts which promote the elimination of hydrohalic acid, such as copper powder, copper and vanadium salts, etc., and with the addition of a hydrogen halide binding agent. In certain cases it is necessary to apply pressure. The new fabrics are valuable for displaying dyes.
The present patent relates to a process for the preparation of Py-1-phenylpyrazolanthrone of the formula
EMI0001.0031
by allowing bromobenzene, pyrazolanthrone and potash to interact in the presence of a small amount of a copper catalyst for the elimination of hydrogen bromide.
<I> Example: </I> Equal parts by weight of pyrazolanthr-one, bromobenzene and potassium carbonate are refluxed for 10 hours with stirring in the presence of a little copper salt in ten times the amount by weight of nitrobenzene. After cooling, it is diluted with fuel, filtered, washed with fuel and water and dried. The resulting phenylpyrazole anthrone crystallizes from glacial acetic acid in beautiful, large yellow crystal needles that melt at 211-212. It should be used for the production of dyes. Concentrated sulfuric acid dissolves with a red color without fluorescence, organic solvents with more or less strong yellow fluorescence.
The same product is formed when pyrazolanthrone and potash are first heated in nitrobenzene until the red potassium salt of pyrazolanthrone is formed and then, after adding bromobenzene and copper, the procedure is continued as described above.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH133473T | 1927-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133473A true CH133473A (en) | 1929-06-15 |
Family
ID=4391622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133473D CH133473A (en) | 1927-10-22 | 1927-10-22 | Process for the preparation of a descendant of the pyrazolanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133473A (en) |
-
1927
- 1927-10-22 CH CH133473D patent/CH133473A/en unknown
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