DE1620247C - 5,8-alkano-5,6,7,8-tetrahydro-lHnaphtho square bracket on 2,3-square bracket to imidazole derivatives and a process for their preparation - Google Patents
5,8-alkano-5,6,7,8-tetrahydro-lHnaphtho square bracket on 2,3-square bracket to imidazole derivatives and a process for their preparationInfo
- Publication number
- DE1620247C DE1620247C DE1620247C DE 1620247 C DE1620247 C DE 1620247C DE 1620247 C DE1620247 C DE 1620247C
- Authority
- DE
- Germany
- Prior art keywords
- alkano
- tetrahydronaphthalene
- tetrahydro
- structural formula
- square bracket
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002460 imidazoles Chemical class 0.000 title description 2
- 229940041158 antibacterial for systemic use Imidazole derivatives Drugs 0.000 title 1
- 229940042051 antimycotic for systemic use Imidazole derivatives Drugs 0.000 title 1
- 229940093910 gyncological antiinfectives Imidazole derivatives Drugs 0.000 title 1
- 229940079865 intestinal antiinfectives Imidazole derivatives Drugs 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000005977 Ethylene Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- YKIOKAURTKXMSB-UHFFFAOYSA-N Adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000001187 sodium carbonate Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- XEIMBIKLKVPYSU-UHFFFAOYSA-N NC1=CC2=C(C=C1N)C1CCC2CC1 Chemical compound NC1=CC2=C(C=C1N)C1CCC2CC1 XEIMBIKLKVPYSU-UHFFFAOYSA-N 0.000 claims 1
- DHGAAPKICSXMST-UHFFFAOYSA-N [O-][N+](=O)C1=CC2=C(C=C1[N+]([O-])=O)C1CCC2CC1 Chemical compound [O-][N+](=O)C1=CC2=C(C=C1[N+]([O-])=O)C1CCC2CC1 DHGAAPKICSXMST-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 230000000202 analgesic Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Dimethyl N aminoantipyrine Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229960000212 aminophenazone Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 1H-naphtho [2,3-d] imidazole compound Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WUIPBXNXSMIKJG-UHFFFAOYSA-N C12=CC=3N=CNC=3C=C2C2CCC1C2 Chemical compound C12=CC=3N=CNC=3C=C2C2CCC1C2 WUIPBXNXSMIKJG-UHFFFAOYSA-N 0.000 description 1
- YOZDIIWLNQIOFN-UHFFFAOYSA-N C1=C(N)C(N)=CC2=C1C1CCC2C1 Chemical compound C1=C(N)C(N)=CC2=C1C1CCC2C1 YOZDIIWLNQIOFN-UHFFFAOYSA-N 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N Morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- OBDHJOMAPSFHDQ-UHFFFAOYSA-N [O-][N+](=O)C1=CC2=C(C=C1[N+]([O-])=O)C1CCC2C1 Chemical compound [O-][N+](=O)C1=CC2=C(C=C1[N+]([O-])=O)C1CCC2C1 OBDHJOMAPSFHDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 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
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229930014694 morphine Natural products 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Description
Gegenstand der Erfindung sind 5,8-Alkano-5,6,7,8-tetrahydro-1 H-naphtho[2,3-d]imidazol-Verbindungen der allgemeinen FormelThe invention relates to 5,8-alkano-5,6,7,8-tetrahydro-1 H-naphtho [2,3-d] imidazole compounds of the general formula
in der R Methylen oder Äthylen ist, und ein Verfahren zu deren Herstellung. Diese Verbindungen sind als schmerzlindernde Mittel brauchbar.wherein R is methylene or ethylene, and a process for their preparation. These connections are useful as pain relievers.
Das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen ist dadurch gekennzeichnet, daß man eine 2,3-Dinitro-5,8-alkano-5,6,7,8-tetrahydronaphthalin-Verbindung der allgemeinen Strukturformel The process for making the invention Compounds is characterized in that a 2,3-dinitro-5,8-alkano-5,6,7,8-tetrahydronaphthalene compound is used the general structural formula
NO2 NO 2
NO,NO,
worin R Methylen oder Äthylen ist, in an sich bekannter Weise reduziert und die erhaltene 2,3-Diamino -5,8 - alkano - 5,6,7,8 - tetrahydronaphthalin -Verbindung der allgemeinen Strukturformel:wherein R is methylene or ethylene, reduced in a manner known per se and the 2,3-diamino obtained -5,8 - alkano - 5,6,7,8 - tetrahydronaphthalene compound of the general structural formula:
NH,NH,
NH,NH,
(II)(II)
worin R die obige Bedeutung hat, in an sich bekannter Weise mit Ameisensäure zu der 5,8-Alkano-5,6,7,8-tetrahydro-1 H-naphtho-[2,3-d]imidazol-Verbindung der allgemeinen Strukturformelwherein R has the above meaning, in a manner known per se with formic acid to give the 5,8-alkano-5,6,7,8-tetrahydro-1 H-naphtho [2,3-d] imidazole compound of the general structural formula
(III)(III)
worin R die obige Bedeutung besitzt, umsetzt.wherein R has the above meaning, converts.
Die Ausgangsverbindung (I) 2,3-Dinitro-5,8-alkano-5,6,7,8-tetrahydronaphthalin ist neu und kann z. B. durch Nitrieren der entsprechenden 5,8-Alkano-5,6,7,8-tetrahydronaphthalin-Verbindung mit einem Gemisch von Salpetersäure und Schwefelsäure hergestellt werdenThe starting compound (I) 2,3-dinitro-5,8-alkano-5,6,7,8-tetrahydronaphthalene is new and can e.g. B. by nitrating the corresponding 5,8-alkano-5,6,7,8-tetrahydronaphthalene compound with a mixture of nitric acid and sulfuric acid
Erfindungsgemäß wird somit die 2,3-Dinitro-SjS-alkano-SjoJjS-tetrahydronaphthalin-Verbindung (I) zunächst für die Umwandlung einer Nitrogruppe in -eine Aminogruppe in üblicher Weise reduziert, z. B. mit Hilfe einer Reaktion unter Verwendung eines Metalls, z. B. Zink, Eisen, Zinn, mit einer Säure oder einem Alkali, unter Verwendung eines Metallhydridkomplexes, z. B. Lithiumaluminiumhydrid, Natriumborhydrid, mit Hilfe einer katalytischen Reduktion unter Verwendung eines Katalysators, z. B. Raney-Nickel, Platindioxyd, oder mit Hilfe einer elektrolytischen Reduktion. Die auf diesem Wege erhaltene 2,3 -Diamin-5,8-alkano-5,6,7,8 -tetrahydronaphthalin-Verbindung (II) wird dann in an sich bekannter Weise mit Ameisensäure, gewöhnlich bei Zimmertemperatur oder unter Erhitzen auf einem Wasserbad, umgesetzt. Diese Reaktionen können mit oder ohne Abtrennung und Reinigung der als Zwischenprodukt erzeugten 2,3-Diamino-5,8-alkano-5,6,7,8-tetrahydronaphthalin-Verbindung (II) vorgeriommen werden. - . 'The 2,3-dinitro-SjS-alkano-SjoJjS-tetrahydronaphthalene compound is thus according to the invention (I) first reduced in the usual way for the conversion of a nitro group into an amino group, z. By means of a reaction using a metal, e.g. B. zinc, iron, tin, with an acid or an alkali, using a metal hydride complex, e.g. B. lithium aluminum hydride, sodium borohydride, by means of catalytic reduction using a catalyst, e.g. B. Raney nickel, platinum dioxide, or with the help of an electrolytic reduction. That way obtained 2,3-diamine-5,8-alkano-5,6,7,8-tetrahydronaphthalene compound (II) is then in a manner known per se with formic acid, usually at room temperature or with heating on a Water bath, implemented. These reactions can be carried out with or without separation and purification of the as Intermediate produced 2,3-diamino-5,8-alkano-5,6,7,8-tetrahydronaphthalene compound (II) to be prepared. -. '
Die so erhaltene S^-Alkano-S^J^-tetrahydro-lH-naphtho[2,3-d]imidazol-Verbindung (III) ist als ein schmerzlinderndes Mittel nützlich. Zum Beispiel ergibt 5j8 - Methano - 5,6,7,8 - tetrahydro -1H - naphtho [2,3-d]imidazol ein ED50 = 33 mg/kg, beim Testieren unter Verwendung einer Maus, gemäß dem Haffner-Verfahren zur Prüfung der schmerzlindernden Wirksamkeit. Die 5,8-Alkano-5,6,7,8-tetrahydro:lH-naphtho[2,3-d]imidazol-Verbindung (III) zeigt eine Inhibition von NF-Sarcom bei Mäusen.The S ^ -alkano-S ^ J ^ -tetrahydro-1H-naphtho [2,3-d] imidazole compound (III) thus obtained is useful as an analgesic. For example, 5j8 - methano - 5,6,7,8 - tetrahydro -1H - naphtho [2,3-d] imidazole gives an ED 50 = 33 mg / kg when tested using a mouse according to Haffner's method for Examination of the pain relieving effectiveness. The 5,8-alkano-5,6,7,8-tetrahydro: 1H-naphtho [2,3-d] imidazole compound (III) shows inhibition of NF sarcoma in mice.
Zur Bestimmung der Toxizität wurden Vergleichsversuche mit dem bekannten Aminophenazon durchgeführt, und es wurden folgende Werte erhalten:To determine the toxicity, comparative tests were carried out with the known aminophenazone, and the following values were obtained:
Akute Toxizitätacute toxicity
Substanz LD50 (mg/kg) MausSubstance LD50 ( m g / kg) mouse
5,8-Äthano-5,6,7,8-tetra-5,8-ethano-5,6,7,8-tetra-
hydro-1 H-naphtho-hydro-1 H-naphtho-
[2,3-d)imidazol 600 (intrap.)[2,3-d) imidazole 600 (intrap.)
5,8-Methano-5,6,7,8-tetra-5,8-methano-5,6,7,8-tetra-
hydro-1 H-naphtho-hydro-1 H-naphtho-
[2,3-d]imidazol 1000 (subk.)[2,3-d] imidazole 1000 (subc.)
Aminophenazon 351 (subk.)Aminophenazon 351 (subc.)
TestverfahrenTest procedure
Die letale Dosis (LD50) wurde wie folgt bestimmt: Die zu prüfenden Substanzen wurden den Mäusen in verschiedenen Einzeldosen subkutan oder intraperitoneal appliziert. Für jede Dosis wurden 10 männliche Mäuse eines Albino-Stammes von 19 bis 21 g Körpergewicht verwendet. Die Testtiere wurden 24 Stunden nach der Gabe der zu prüfenden Substanzen beobachtet.The lethal dose (LD 50 ) was determined as follows: The substances to be tested were administered subcutaneously or intraperitoneally to the mice in various individual doses. For each dose, 10 male mice of an albino strain of 19 to 21 g body weight were used. The test animals were observed 24 hours after the administration of the substances to be tested.
In der nachfolgenden Tabelle werden die analgetische
Aktivität und die akute Toxizität der Vergleichsverbindung Aminophenazon mit den entsprechenden
Angaben des S^-Methano-Sjo^Shd
1 H-naphtho[2,3-d]imidazols verglichenIn the table below, the analgesic activity and the acute toxicity of the comparison compound aminophenazone with the corresponding information from the S ^ -Methano-Sjo ^ Shd
1 H-naphtho [2,3-d] imidazoles compared
VerbindungtJ - - ■
connection
5,6,7,8-tetrahydro-
1 H-naphtho[2,3-d]-
imidazol5,8-methano-
5,6,7,8-tetrahydro-
1 H-naphtho [2,3-d] -
imidazole
phenazonAmino
phenazone
ED50 (mg/kg)
Akute Toxizität
LD50 (mg/kg) 50 Analgesic Activity
ED 50 (mg / kg)
acute toxicity
LD 50 (mg / kg)
100033
1000
33586
335
Die akute Toxizität (LD50) wurde bei intraperitonealer Verabreichung nach der bereits oben der vorliegenden Beschreibung geschilderten Methode bestimmt.The acute toxicity (LD 50 ) was determined with intraperitoneal administration according to the method already described above in the present description.
Die analgetische Aktivität (ED50) wurde wie folgt ermittelt: Als Testtiere verwendete man weiße Mäuse mit einem Gewicht von 19 bis 21g, jede Gruppe bestand aus' 10 Mäusen. Die Testtiere ,wurden intraperitoneal mit einer bestimmten Menge Testverbindung und 3,5 mg Morphin pro Kilogramm Körpergewicht behandelt. Nach 30 Minuten wurde nut einer Pinzette in den Schwanz gekniffen, um zu sehen, ob er rasch weggezogen wird. Die wirksame Dosis 50 (ED50) wurde nach der Bliss-Methode berechnet.The analgesic activity (ED 50 ) was determined as follows: white mice weighing 19 to 21 g were used as test animals, each group consisted of 10 mice. The test animals were treated intraperitoneally with a certain amount of test compound and 3.5 mg of morphine per kilogram of body weight. After 30 minutes, tweezers were used to pinch the tail to see if it was pulled away quickly. The effective dose 50 (ED 50 ) was calculated using the Bliss method.
Das oben beschriebene Verfahren zur Herstellung der erfindungsgemäßen Verbindungen wird mit einigen Beispielen näher erläutert.The above-described process for preparing the compounds of the invention will work with some Examples explained in more detail.
Zu einer Lösung von 1,01 g 2,3-Dinitro-5,8-methano-5,6,7,8-tetrahydronaphthalin in 50 ml Äthylacetat werden 0,09 g Platindioxyd zugegeben, und es wird Wasserstoffgas in das erhaltene Gemisch unter Schütteln eingeführt. Nach Absorbieren von 650 ml innerhalb von 1% Stunden wird das Reaktionsgemisch filtriert, zwecks Entfernung des Katalysators, und unter vermindertem Druck eingeengt, wobei 2,3-Diamino-5,8-methano-5,6,7,8-tetrahydronaphthalin in Form eines gelben Feststoffes erhalten wird. Der Feststoff wird mit 5 ml Ameisensäure vermengt und auf einem Dampfbad während 2 Stunden erhitzt. Das Reaktionsgemisch wird dann auf Eis geschüttet, mit Natriumcarbonat alkalisch gemacht und mit Äther geschüttelt. Die Ätherschicht wird dann mit Wasser gewaschen, über wasserfreiem Natriumsulfat getrocknet, und es wird das Lösungsmittel entfernt. Der Rückstand wird aus Benzol kristallisiert und liefert 0,51 g 5,8-Methano-5,6,7,8 - tetrahydro -1H - naphtho[2,3 - d]imidazol in Form von Kristallen mit F = 198,5 bis 199,5° C.To a solution of 1.01 g of 2,3-dinitro-5,8-methano-5,6,7,8-tetrahydronaphthalene in 50 ml of ethyl acetate, 0.09 g of platinum dioxide is added, and hydrogen gas is introduced into the resulting mixture Shaking introduced. After absorbing 650 ml within 1% hour, the reaction mixture is filtered in order to remove the catalyst, and concentrated under reduced pressure, whereby 2,3-diamino-5,8-methano-5,6,7,8-tetrahydronaphthalene in the form a yellow solid is obtained. The solid is mixed with 5 ml of formic acid and heated on a steam bath for 2 hours. The reaction mixture is then poured onto ice, made alkaline with sodium carbonate and shaken with ether. The ether layer is then washed with water, dried over anhydrous sodium sulfate, and the solvent is removed. The residue is crystallized from benzene and yields 0.51 g of 5,8-methano-5,6,7,8-tetrahydro -1H-naphtho [2,3-d] imidazole in the form of crystals with F = 198.5 bis 199.5 ° C.
Analyse für C12H12N2:Analysis for C 12 H 12 N 2 :
Berechnet ..
gefunden ...Calculated ..
found ...
C 78,23, H 6,57, N 15,21;
C 78,30, H 6,70, N 15,06.C 78.23, H 6.57, N 15.21;
C 78.30, H 6.70, N 15.06.
wird das Lösungsmittel entfernt. Der erhaltene Rückstand wird aus Benzol kristallisiert und man erhält 0,87 g 5,8 - Äthano - 5,6,7,8 - tetrahydro - 1 H - naphtho[2,3-d]imidazol in Form von Kristallen mit F. = 227 bis 228° C.the solvent is removed. The residue obtained is crystallized from benzene and is obtained 0.87 g of 5.8 - ethano - 5,6,7,8 - tetrahydro - 1 H - naphtho [2,3-d] imidazole in the form of crystals with F. = 227 to 228 ° C.
Analyse für C13H14N2:Analysis for C 13 H 14 N 2 :
Berechnet ... C 78,75, H 7,12, N 14,13;
gefunden .... C 78,57, H 7,17, N 14,24.Calculated ... C 78.75, H 7.12, N 14.13;
found .... C 78.57, H 7.17, N 14.24.
Claims (2)
Family
ID=
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