CH296571A - Process for the preparation of 1,10-phenanthroline-5,6-quinone. - Google Patents
Process for the preparation of 1,10-phenanthroline-5,6-quinone.Info
- Publication number
- CH296571A CH296571A CH296571DA CH296571A CH 296571 A CH296571 A CH 296571A CH 296571D A CH296571D A CH 296571DA CH 296571 A CH296571 A CH 296571A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- phenanthroline
- preparation
- parts
- quinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- KCALAFIVPCAXJI-UHFFFAOYSA-N 1,10-phenanthroline-5,6-dione Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CN=C3C2=N1 KCALAFIVPCAXJI-UHFFFAOYSA-N 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- SQNBCNWXJSODLJ-UHFFFAOYSA-N 5-methoxy-1,10-phenanthroline Chemical compound C1=CC=C2C(OC)=CC3=CC=CN=C3C2=N1 SQNBCNWXJSODLJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000003569 amebicidal effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung von 1,10-Phenanthrolin.5,6-eMnon. CTegenstand des vorliegenden Patentes ist ein neues Verfahren zur Herstellung von 1..10-Pheiianthrolin-5,6-ehinon, welehes da durch gekennzeichnet ist, dass man eine Ver bindung der Formel
EMI0001.0006
worin Y einen durch Oxydation in die Oxo- gruppe überführbaren Substituenten,
wie eine freie oder verätherte Oxygruppe oder eine Freie oder acylierte Aminogruppe, darstellt, mit Salpetersäure oxydiert.
Das so erhaltene 1,10-Phenanthrolin-5,6- chinon der Formel
EMI0001.0019
schmilzt bei 250 . Es besitzt amoebicide Wir kung und soll als Heilmittel oder als Zwi schenprodukt zur Herstellung von Heilmitteln verwendet werden.
Die Oxydation mit. Salpetersäure wird vor zugsweise in Gegenwart von Schwefelsäure bei erhöhter Temperatur, z. B. 50 bis 150 , durch geführt.
Beispiel.: 1 Gewichtsteil 5-Methoxy-1,10-plienairthro- lin wird mit 5 Volumteilen konz. Sehwefel- säure und unter Kühlung mit 3 Volumteilen rauchender Salpetersäure (d = 1,51) versetzt und während 11/2 Stunden auf 120 erhitzt. Hierauf wird die Reaktionslösung auf Eis gegossen und unter Eiskühlung mit 10n-Na- tronlauge auf pH 6 gestellt.
Die wässerige Lö sung wird auf 30 Volumteile eingeengt und mit 500 Volumteilen warmem Chloroform aus gezogen. Nach Abdampfen des Chloroforms bleiben rötliche Kristalle zurück, die aus Me thylalkohol umkristallisiert werden. Man er hält so das 1,10-Phenanthroliil-5,6-chinon der Formel
EMI0001.0037
in gelblichen Kristallen vom F. = 250 .
Das 5-Methoxy-1,10-phenanthrolin lässt sich zum Beispiel auf folgendem Wege dar stellen 10 Gewichtsteile 5-Cliloi--1,10-plienanthro- lin werden mit 4 Gewichtsteilen Kaliiun- hydroxyd, 1 Gewichtsteil Naturkupfer und 50 Volumteilen abs. Methanol während 8 Stun den im verschlossenen Rohr auf 160 erhitzt.
Hierauf destilliert man den Methylalkohol ab, zieht den Rückstand mit 200 Volumteilen 2n Salzsäure aus, nutscht von Verunreinigiiin- gen ab, macht mit Natronlauge alkalisch und schüttelt die wässerige Lösung mit 750 Vo- lumteilen Chloroform aus. Durch LTmkristal-
EMI0002.0001
lisat.ion <SEP> des <SEP> Rückstandes <SEP> 'aus <SEP> Essigester <SEP> Will-(1
<tb> das <SEP> 5---#letliox@--1,1.0-plienanthrolin <SEP> in <SEP> weissen
<tb> Kristallen <SEP> vom <SEP> F. <SEP> = <SEP> 104 <SEP> bis <SEP> 105 <SEP> erhalten.
Process for the preparation of 1,10-phenanthroline,5,6-emnone. The subject matter of the present patent is a new process for the production of 1..10-Pheiianthrolin-5,6-ehinone, which is characterized by the fact that one has a compound of the formula
EMI0001.0006
where Y is a substituent which can be converted into the oxo group by oxidation,
such as a free or etherified oxy group or a free or acylated amino group, is oxidized with nitric acid.
The 1,10-phenanthroline-5,6-quinone of the formula obtained in this way
EMI0001.0019
melts at 250. It has an amoebicidal effect and is intended to be used as a remedy or as an intermediate product in the manufacture of remedies.
The oxidation with. Nitric acid is preferably used in the presence of sulfuric acid at an elevated temperature, for. B. 50 to 150 performed.
Example: 1 part by weight of 5-methoxy-1,10-plienairthro- lin is concentrated with 5 parts by volume. Sulfuric acid and, while cooling, 3 parts by volume of fuming nitric acid (d = 1.51) were added and the mixture was heated to 120 for 11/2 hours. The reaction solution is then poured onto ice and adjusted to pH 6 with 10N sodium hydroxide solution while cooling with ice.
The aqueous solution is concentrated to 30 parts by volume and drawn off with 500 parts by volume of warm chloroform. After the chloroform has evaporated, reddish crystals remain, which are recrystallized from methyl alcohol. So he keeps the 1,10-phenanthroliil-5,6-quinone of the formula
EMI0001.0037
in yellowish crystals of F. = 250.
The 5-methoxy-1,10-phenanthroline can be represented, for example, in the following way: 10 parts by weight of 5-Cliloi - 1,10-plienanthroline are mixed with 4 parts by weight of potassium hydroxide, 1 part by weight of natural copper and 50 parts by volume of abs Methanol was heated to 160 in the sealed tube for 8 hours.
The methyl alcohol is then distilled off, the residue is extracted with 200 parts by volume of 2N hydrochloric acid, impurities are suctioned off, made alkaline with sodium hydroxide solution and the aqueous solution is extracted with 750 parts by volume of chloroform. By LTmkristal-
EMI0002.0001
lisat.ion <SEP> of the <SEP> residue <SEP> 'from <SEP> ethyl acetate <SEP> Will- (1
<tb> das <SEP> 5 --- # letliox @ - 1,1.0-plienanthrolin <SEP> in <SEP> white
<tb> Crystals <SEP> received from <SEP> F. <SEP> = <SEP> 104 <SEP> to <SEP> 105 <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH293298T | 1950-05-05 | ||
| CH296571T | 1950-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296571A true CH296571A (en) | 1954-02-15 |
Family
ID=25733345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296571D CH296571A (en) | 1950-05-05 | 1950-05-05 | Process for the preparation of 1,10-phenanthroline-5,6-quinone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296571A (en) |
-
1950
- 1950-05-05 CH CH296571D patent/CH296571A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH296571A (en) | Process for the preparation of 1,10-phenanthroline-5,6-quinone. | |
| DE1083830B (en) | Process for the preparation of 3-aminothiophene-2-carboxylic acid esters or the corresponding free carboxylic acids | |
| DE921265C (en) | Process for the preparation of aryl-substituted pyrazoline compounds | |
| AT219204B (en) | Process for the preparation of 3-alkoxy-19-nor-δ <2,5 (10)> -androstadien-17-one | |
| AT218527B (en) | Process for making new hydrazones | |
| CH205160A (en) | Method for producing a capillary-active connection. | |
| CH309830A (en) | Process for producing a hydrazine compound. | |
| CH293298A (en) | Process for the preparation of a new phenanthroline quinone. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH310724A (en) | Process for the production of a new Schiff base. | |
| CH296573A (en) | Process for the preparation of a new phenanthroline quinone. | |
| CH127177A (en) | Process for the preparation of isopropylisopropenylpropargylbarbituric acid. | |
| CH353006A (en) | Process for the preparation of 3-low molecular weight alkoxy-19-nor- ^ 2.5 (10) -androstadien-17-one compounds | |
| CH212591A (en) | Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. | |
| DE1201341B (en) | Process for the saponification of organic esters of 3-keto-17beta-hydroxy-13beta-alkyl-A4-gene | |
| CH296572A (en) | Process for the preparation of a new phenanthroline quinone. | |
| CH244769A (en) | Process for the preparation of a sulfuric acid ester. | |
| CH243019A (en) | Process for the preparation of a basic ester. | |
| DE1079024B (en) | Process for the production of 3-carbamyl-4-methyl-novobiose | |
| CH284987A (en) | Process for preparing 5,6-3B-acetoxy-11-keto-etiocholenic acid. | |
| CH156308A (en) | Process for the preparation of a sulfuric acid ester. | |
| CH269085A (en) | Process for the preparation of a new hydrazine compound. | |
| CH310726A (en) | Process for the production of a new Schiff base. | |
| CH310728A (en) | Process for the production of a new Schiff base. | |
| CH306287A (en) | Process for the preparation of a piperidine derivative. |