CH199450A - Process for the preparation of an oxyperinaphthindanedione. - Google Patents
Process for the preparation of an oxyperinaphthindanedione.Info
- Publication number
- CH199450A CH199450A CH199450DA CH199450A CH 199450 A CH199450 A CH 199450A CH 199450D A CH199450D A CH 199450DA CH 199450 A CH199450 A CH 199450A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxyperinaphthindanedione
- reaction
- water
- carried out
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- -1 malonate ester Chemical class 0.000 claims 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Ogyperinaphthindandions. Es wurde gefunden, dass 5-Oxyperinaph- thindandion hergestellt werden kann, wenn 3 -Oxynaphthalin-1,8 - dicarbonsäureanhydrid mit Malonsäureestern umgesetzt wird.
Das neue 5-Oxyperinaphthindandion stellt ein hellgelbes Pulver dar, das bei etwa 260 unter Zersetzung schmilzt. Es ist in Wasser unlöslich, dagegen leicht löslich in verdünn ter Sodalösung und stellt ein wertvolles Zwi schenprodukt zur Herstellung von Farb stoffen, sowie von pharmazeutischen Pro dukten dar.
Die Umsetzung mit Malonsäureestern wird zweckmässig so vorgenommen, dass das 3-Ogynaphthalin-1,8-dicarbonsäureanhydrid mit beispielsweise Malonsäurediäthylester auf höhere Temperatur, beispielsweise 150 bis <B>250'</B> erhitzt wird, wobei in Gegenwart in differenter Lösungs- oder Verdünnungsmittel gearbeitet werden kann und mit Vorteil Kon densationsmittel, wie z. B. Zinkchlorid, zur Beschleunigung der Reaktion zugefügt wer den.
<I>Beispiel:</I> Man mischt 150 Teile 3-Oxynaphthalin- 1,8-dicarbonsäureanhydrid, 160 Teile frisch geschmolzenes, fein pulverisiertes Zink chlorid, sowie 300 Teile Malonsäurediäthyl- ester und erhitzt 5 Stunden auf 175 bis 185 . Nach dem Erkalten wird das Reak tionsprodukt mit Wasser gemahlen, filtriert und mit Wasser so lange gewaschen, bis im Waschwasser keine Zinkionen mehr nach weisbar sind. Man löst den Rückstand unter Zugabe von Ammoniak bis zur schwach alkalischen Reaktion in 1000 Teilen Wasser, filtriert von ungelösten Bestandteilen ab und säuert das Filtrat mit Salzsäure an.
Das 5-Oxyperinaphthindandion (Bezifferung der Substitutionsstellen siehe Beilsteins Hand buch, IV. Auflage, Ergänzungswerk, VII. Band, Seite 391) wird filtriert, mit Wasser gewaschen und getrocknet.
Process for the preparation of an ogyperinaphthindandione. It has been found that 5-oxyperinaphthindanedione can be produced if 3-oxynaphthalene-1,8-dicarboxylic acid anhydride is reacted with malonic acid esters.
The new 5-oxyperinaphthindanedione is a light yellow powder that melts with decomposition at about 260. It is insoluble in water, but slightly soluble in dilute soda solution and is a valuable intermediate product in the manufacture of dyes and pharmaceutical products.
The reaction with malonic acid esters is expediently carried out in such a way that the 3-ogynaphthalene-1,8-dicarboxylic anhydride is heated to a higher temperature, for example 150 to 250 ', with, for example, malonic acid diethyl ester, in the presence of different solvents or Diluent can be worked and with advantage condensation agents such. B. zinc chloride, added to accelerate the reaction who the.
<I> Example: </I> 150 parts of 3-oxynaphthalene-1,8-dicarboxylic anhydride, 160 parts of freshly melted, finely powdered zinc chloride, and 300 parts of diethyl malonate are mixed and heated to 175 to 185 for 5 hours. After cooling, the reaction product is ground with water, filtered and washed with water until no more zinc ions can be detected in the wash water. The residue is dissolved in 1000 parts of water with the addition of ammonia until a weakly alkaline reaction occurs, undissolved constituents are filtered off and the filtrate is acidified with hydrochloric acid.
The 5-oxyperinaphthindanedione (for numbering of the substitution sites see Beilstein's handbook, 4th edition, supplementary work, VII. Volume, page 391) is filtered, washed with water and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199450T | 1937-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199450A true CH199450A (en) | 1938-08-31 |
Family
ID=4441839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199450D CH199450A (en) | 1937-05-18 | 1937-05-18 | Process for the preparation of an oxyperinaphthindanedione. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199450A (en) |
-
1937
- 1937-05-18 CH CH199450D patent/CH199450A/en unknown
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