CH185571A - Process for the preparation of an aminochrysenic sulfonic acid. - Google Patents
Process for the preparation of an aminochrysenic sulfonic acid.Info
- Publication number
- CH185571A CH185571A CH185571DA CH185571A CH 185571 A CH185571 A CH 185571A CH 185571D A CH185571D A CH 185571DA CH 185571 A CH185571 A CH 185571A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- sulfonic acid
- aminochrysenic
- acetamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title description 2
- -1 acetamino-aminochrysene Chemical compound 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- MWKMQUZZZYRXBN-UHFFFAOYSA-N 2-aminochrysene-1-sulfonic acid Chemical compound NC1=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C=C1)S(=O)(=O)O MWKMQUZZZYRXBN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IHRSMKQFWZZOLX-UHFFFAOYSA-N 2,3-diaminochrysene-1-sulfonic acid Chemical compound NC=1C(=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C1)S(=O)(=O)O)N IHRSMKQFWZZOLX-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Aminochrysensulfosäur e. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Darstellung einer Aminochrysensulfosäure, welches da durch gekennzeichnet ist, dass man Acet- amino-aminochrysen vom Schmelzpunkt 266 bis 268 C mit einem sulfonierend wirken den Mittel behandelt.
<I>Beispiel:</I> 20 Gewichtsteile Acetamino-aminochry- sen vom Schmelzpunkt 266 bis<B>268'</B> C wer den in 800 Gewichtsteilen :Schwefelsäure monohydrat 3 bis 4 Stunden bei 45 bis<B>50'</B> C verrührt. Man gibt auf Eis, Saugt ab, löst in Natriumcarbonat und filtriert. Mit Na triumchlorid fällt die Diaminochrysensulfo- säure aus.
Die so erhaltene Diaminochrysen- sulfosäure kristallisiert aus Wasser in schwach gelb gefärbten Blättchen. Diazotiert man diese Diaminochrysensulfosäure und gibt sie in alkalische Naphtollösung, so er hält man einen blauvioletten Farbstoff. Sie kann zur Darstellung von Farbstoffen und pharmazeutischen Produkten Verwendung finden.
Das als Ausgangsstoff verwendete Acet- amino-aminochrysen kann folgendermassen erhalten werden: Acetaminochrysen vom Schmelzpunkt 286 bis<B>288'</B> C wird in Eisessig suspendiert und mit Salpetersäure vom spezifischen Ge wicht 1,5 bei etwa 70 bis 80 C nitriert. Das so erhaltene Nitroprodukt wird in Pyridin in Gegenwart von fein verteiltem Nickel in einem Autoklaven bei 70 bis 90 mit Was serstoff reduziert.
Hierdurch wird das @Acet- amino-aminochrysen, das sich aus Eisessig umkristallisieren lässt, erhalten.
Method for the preparation of an aminochrysensulfonic acid e. The subject of the present Zusatzpa tentes is a method for the preparation of an aminochrysenic sulfonic acid, which is characterized in that acetamino-aminochrysene with a melting point of 266 to 268 C is treated with a sulfonating agent.
<I> Example: </I> 20 parts by weight of acetamino-aminochrysene with a melting point of 266 to <B> 268 '</B> C are used in 800 parts by weight: sulfuric acid monohydrate 3 to 4 hours at 45 to <B> 50' </B> C stirred. It is poured onto ice, suctioned off, dissolved in sodium carbonate and filtered. The diaminochrysensulphonic acid precipitates with sodium chloride.
The diaminochrysenesulfonic acid obtained in this way crystallizes from water in pale yellow colored flakes. If you diazotise this diaminochrysene sulfonic acid and put it in alkaline naphthol solution, you get a blue-violet dye. It can be used to represent dyes and pharmaceutical products.
The acetaminochrysenic used as the starting material can be obtained as follows: Acetaminochrysenic with a melting point of 286 to 288 ° C is suspended in glacial acetic acid and nitrated with nitric acid with a specific weight of 1.5 at about 70 to 80 ° C . The nitro product thus obtained is reduced in pyridine in the presence of finely divided nickel in an autoclave at 70 to 90 with hydrogen.
The @acet-amino-aminochrysen, which can be recrystallized from glacial acetic acid, is obtained in this way.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE179446X | 1933-12-15 | ||
| DE185571X | 1933-12-15 | ||
| CH179447T | 1934-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185571A true CH185571A (en) | 1936-07-31 |
Family
ID=27177660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185571D CH185571A (en) | 1933-12-15 | 1934-12-13 | Process for the preparation of an aminochrysenic sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185571A (en) |
-
1934
- 1934-12-13 CH CH185571D patent/CH185571A/en unknown
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