CH160943A - Process for the preparation of a naphthoylene-naphtimidazole-peridicarboxylic acid. - Google Patents
Process for the preparation of a naphthoylene-naphtimidazole-peridicarboxylic acid.Info
- Publication number
- CH160943A CH160943A CH160943DA CH160943A CH 160943 A CH160943 A CH 160943A CH 160943D A CH160943D A CH 160943DA CH 160943 A CH160943 A CH 160943A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- naphtimidazole
- preparation
- naphthoylene
- solution
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Darstellung einer Naphtoylen-naphtimidazol-perl-dikarbonsäure. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Darstellung einer Naphtoylen- naphtimidazol-peridikarbonsäure, für welche eine der folgenden Formeln in Betracht fällt:
EMI0001.0004
welches dadurch gekennzeichnet ist, dass man das Di-Kaliumsalz der 1 .4. 5 .8-Naphtalin- tetrakarbonsäure mit 1.2-Diaminonaphtalin zur Umsetzung bringt.
Die neue Verbindung ist ein wertvolles Zwischenprodukt für die Darstellung von Farbstoffen. <I>Beispiel:</I> 15 Gewichtsteile 1.4.5.8-Naphtalin- tetrakarbonsäure werden in Wasser suspen diert und mit etwa 7-8 Teilen Kalium karbonat in Lösung gebracht. Die auf diese Weise dargestellte Lösung des Dikalium- salzes wird zum Sieden erhitzt, zu der sieden den Lösung werden nach und nach 8-9 Ge wichtsteile 1.2-Diaminonaphtalin gegeben; das Reaktionsgemisch wird hierauf - noch mehrere Stunden im Sieden erhalten.
Die Lösung wird dann von einer geringen Menge eines unlöslichen Produktes, welches wahr scheinlich ein durch doppelte Umsetzung ge bildetes Di-Naphtimidazol ist, durch Filtrieren befreit. Das Filtrat wird in der Siedehitze mit soviel konzentrierter Salzsäure versetzt, dass die gebildete Naphtoylen-naphtimidazol- peridikarbonsäure ausgefällt wird, die etwa nicht umgesetzte Naphtalintetrakarbonsäure aber noch in Lösung bleibt. Das Reaktions produkt wird isoliert und getrocknet. Es stellt ein braunes Pulver dar, das sich in konzentrierter Schwefelsäure mit rotvioletter Farbe löst. Die Lösung des Natriumsalzes ist gelb.
Ihr Anhydrid gibt mit Alkali und Hydrostilfit in der Kälte eine unbeständige grüne Lösung.
Process for the preparation of a naphthoylene-naphtimidazole-perl-dicarboxylic acid. The subject of this additional patent is a process for the preparation of a naphthoylene naphtimidazole peridicarboxylic acid, for which one of the following formulas is possible:
EMI0001.0004
which is characterized in that the di-potassium salt of 1 .4. Brings 5 .8-naphthalene tetracarboxylic acid with 1,2-diaminonaphthalene to implement.
The new compound is a valuable intermediate for the preparation of dyes. <I> Example: </I> 15 parts by weight of 1.4.5.8-naphthalene tetracarboxylic acid are suspended in water and dissolved with about 7-8 parts of potassium carbonate. The solution of the dipotassium salt prepared in this way is heated to the boil, to which the boiling solution is gradually added 8-9 parts by weight of 1,2-diaminonaphthalene; the reaction mixture is then boiled for several hours.
The solution is then freed from a small amount of an insoluble product which is likely to be a di-naphthimidazole formed by double reactions, by filtration. Concentrated hydrochloric acid is added to the filtrate at the boiling point so that the naphthoylene-naphtimidazole peridicarboxylic acid formed is precipitated, but any unreacted naphthalene tetracarboxylic acid still remains in solution. The reaction product is isolated and dried. It is a brown powder that dissolves in concentrated sulfuric acid with a red-violet color. The solution of the sodium salt is yellow.
Your anhydride, together with alkali and Hydrostilfit, gives an unstable green solution in the cold.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE160943X | 1930-09-05 | ||
| CH155775T | 1931-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH160943A true CH160943A (en) | 1933-03-31 |
Family
ID=25716637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH160943D CH160943A (en) | 1930-09-05 | 1931-08-25 | Process for the preparation of a naphthoylene-naphtimidazole-peridicarboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH160943A (en) |
-
1931
- 1931-08-25 CH CH160943D patent/CH160943A/en unknown
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