DE285637C - - Google Patents
Info
- Publication number
- DE285637C DE285637C DENDAT285637D DE285637DA DE285637C DE 285637 C DE285637 C DE 285637C DE NDAT285637 D DENDAT285637 D DE NDAT285637D DE 285637D A DE285637D A DE 285637DA DE 285637 C DE285637 C DE 285637C
- Authority
- DE
- Germany
- Prior art keywords
- percent
- quinoline
- general formula
- oxime
- found
- 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.)
- Active
Links
- 150000002923 oximes Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- -1 Quinolyl alkyl ketones Chemical class 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OSJLYUIRCUMENX-UHFFFAOYSA-N 1-quinolin-2-ylethanamine Chemical compound C1=CC=CC2=NC(C(N)C)=CC=C21 OSJLYUIRCUMENX-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVi 285637 KLASSE Mp. GRUPPE- JVI 285637 CLASS GROUP Mp.
in FRANKFURT a. M.in FRANKFURT a. M.
Verfahren zur Darstellung von ω-Aminoalkylchinolinen. Zusatz zum Patent 279193.Process for the preparation of ω-aminoalkylquinolines. Addendum to patent 279193.
Patentiert im Deutschen Reiche vom 9. Dezember 1913 ab. Längste Dauer: 5. März 1928.Patented in the German Empire on December 9, 1913. Longest duration: March 5, 1928.
Durch das Hauptpatent 279193 ist ein Verfahren zur Herstellung von u -Aminomethylchinolinen der allgemeinen Formel:The main patent 279193 describes a process for the preparation of u-aminomethylquinolines the general formula:
R-CH2-NH2,R-CH 2 -NH 2 ,
in der R den Rest des Chinolins oder eines substituierten Chinolins bedeutet, geschützt, welches darin besteht, daß man Nitrile der Chinolinreihe unter Benutzung üblicher Methoden reduziert.in which R denotes the remainder of the quinoline or a substituted quinoline, protected, which consists in treating quinoline series nitriles using conventional methods reduced.
Es wurde nun gefunden, daß man nach den gleichen Arbeitsweisen andere ω-Aminoalkylchinoline gewinnen kann.It has now been found that other ω-aminoalkylquinolines can be obtained by the same procedures can win.
Amine von der allgemeinen Formel:Amines of the general formula:
Rl>CH.NH2,
Rn Rl > CH.NH 2 ,
Marg
in der Ri den Rest des Chinolins oder eines substituierten Chinolins und Rn den Rest eines Alkyls oder eines substituierten Alkyls bedeutet, sind bisher noch nicht dargestellt worden. Nach Maßgabe der Erfindung erhält man diese Körper, wenn man Oxime von Chinolylalkylketonen der allgemeinen Formel:in which Ri denotes the remainder of the quinoline or a substituted quinoline and R n denotes the remainder of an alkyl or a substituted alkyl have not yet been shown. According to the invention, these bodies are obtained when oximes of quinolyl alkyl ketones of the general formula:
Kl>C
Rn Kl > C
Marg
NOHNOH
den üblichen Reduktionsmethoden unterwirft.subject to the usual reduction methods.
I. Beispiel.
4 · a-Aminoäthyl-6-methoxychinolin.I. Example.
4 α-aminoethyl-6-methoxyquinoline.
Als Ausgangsstoff dient das hisher noch nicht dargestellte Oxim des 6-Methoxychinolyl-4-methylketons (Ber. 45 [1912], S. 3098), dessen salzsaures Salz bei der Umsetzung des 6-Methoxychinolyl-4-methylketons mit salzsaurem Hydroxylamin in methylalkoholischer Lösung entsteht. Das aus dem Chlorhydrat durch Natriumcarbonat in Freiheit gesetzte Oxim schmilzt unscharf bei 142 bis 150 °.The starting material used is the oxime of 6-methoxyquinolyl-4-methyl ketone, which has not yet been shown (Ber. 45 [1912], p. 3098), its hydrochloric acid salt in the reaction of 6-methoxyquinolyl-4-methyl ketone with hydrochloric acid hydroxylamine in methyl alcoholic solution. That from the chlorohydrate through Oxime released from sodium carbonate melts indistinctly at 142 to 150 °.
Für:For:
berechnet:calculated:
C = 66,66 Prozent,
H= 5,55 -C = 66.66 percent,
H = 5.55 -
C12H12O2N2 C 12 H 12 O 2 N 2
gefunden:found:
C = 66,4 Prozent,
H= 5,3 - -C = 66.4 percent,
H = 5.3 - -
Eine Lösung dieses Oxims in Alkohol wird bei Gegenwart von 2V2 Äquivalenten Salzsäure mit Palladiumschwarz und elementarem Wasserstoff unter einem Überdruck von 1Z10 Atm. so lange auf der Schüttelmaschine behandelt, bis die berechnete Menge Wasserstoff (auf ι Mol. Oxim 4 Atome Wasserstoff) absorbiert ist. Das Filtrat wird zur Trockne eingedampft und das rückständige Chlorhydrat aus Wasser unter Zusatz von Salzsäure umkristallisiert.A solution of this oxime in alcohol is in the presence of 2V 2 equivalents of hydrochloric acid with palladium black and elemental hydrogen under a pressure of 1 Z 10 atm. Treated on the shaker until the calculated amount of hydrogen (per ι mol. Oxime 4 atoms of hydrogen) is absorbed. The filtrate is evaporated to dryness and the residual hydrochloric acid is recrystallized from water with the addition of hydrochloric acid.
Man erhält so als schwerlösliches Salz (nichtAs a sparingly soluble salt (not
das Di-, sondern) das Monochlorhydraf des 4· a-Aminoäthyl-6-methoxychinolins in weißen, seideglänzenden, verfilzten Nädelchen, welche bei 234 bis 235 ° unter Zersetzung schmelzen.the di-, but) the monochlorohydraf des 4 a-aminoethyl-6-methoxyquinolines in white, shiny, matted needles, which melt at 234 to 235 ° with decomposition.
Für: C12H14ON2, HClFor: C 12 H 14 ON 2 , HCl
berechnet: gefunden:calculated: found:
Cl = 14,88 Prozent, Cl = 14,80 Prozent.
10 Cl = 14.88 percent, Cl = 14.80 percent.
10
Die aus dem Salz mittels Natronlauge und Äther abgeschiedene freie Base:The free base separated from the salt using caustic soda and ether:
CH (NH2). CH3 CH (NH 2 ). CH 3
CH3 Ο--«CH 3 Ο-- «
bildet ein hellgelbes, grün fluoreszierendes öl, das unter einem Druck von 2 mm bei 169 bis 171 ° (Quecksilberfaden ganz in Dampf) übergeht. forms a light yellow, green fluorescent oil, which under a pressure of 2 mm at 169 to 171 ° (mercury thread turns completely into vapor).
C1214 C 1214
gefunden:found:
C = 71,08 Prozent,
H= 7,07C = 71.08 percent,
H = 7.07
Für:For:
berechnet:
C = 71,28 Prozent,
6,93 -calculated:
C = 71.28 percent,
6.93 -
12H14ON2 12 H 14 ON 2
H =H =
II. Beispiel.II. Example.
2 · a-Aminoäthylchinolin.2 · α-aminoethylquinoline.
Zur Darstellung dieses Carbinamins geht man von dem bisher nicht beschriebenen Oxim des Chinonyl-2-methylketons aus (vgl. Ber. 46 [1913], S. 2931).For the preparation of this carbinamine one starts from the so far not described oxime of quinonyl-2-methyl ketone (cf. Ber. 46 [1913], p. 2931).
Dieses Oxim wird in der üblichen Weise durch Umsetzung des Ketons mit salzsaurem Hydroxylamin bereitet. Sein s'alzsaures Salz schmilzt bei 226 °.This oxime is produced in the usual way by reacting the ketone with hydrochloric acid Preparing hydroxylamine. Its acidic salt melts at 226 °.
Für: C11H10ON21HClFor: C 11 H 10 ON 21 HCl
berechnet: gefunden:calculated: found:
Cl = 15,95 Prozent, CI = 15,83 Prozent.Cl = 15.95 percent, CI = 15.83 percent.
Das unter Benutzung der im I. Beispiel beschriebenen Arbeitsweise reduzierte Oximchlorhydrat liefert das Dichlorhydrat des 2 · a-Aminoäthylchinolins vom Snip. 213 bis 214°.The oxime chlorohydrate reduced using the procedure described in Example I. supplies the dichlorohydrate of 2 a-aminoethylquinoline from Snip. 213 to 214 °.
Für: C11H12N2, 2 HClFor: C 11 H 12 N 2 , 2 HCl
berechnet: gefunden:calculated: found:
Cl = 28,98 Prozent, Cl = 28,72 Prozent.Cl = 28.98 percent, Cl = 28.72 percent.
Das dem Salz zugrunde liegende 2 · a-Aminoäthylchinolin :The 2 a-aminoethylquinoline on which the salt is based:
-CH (NH2) · CHa -CH (NH 2 ) • CH a
siedet unter einem Druck von ι mm bei 125 bis (Faden ganz im Dampf) und erstarrt allmählich zu einer farblosen kristallinischen Masse.boils under a pressure of ι mm at 125 to (Thread entirely in the steam) and gradually solidifies to a colorless crystalline Dimensions.
Für: C11H12N2 For: C 11 H 12 N 2
berechnet:calculated:
C = 76,74 Prozent,
H= 6,97 -C = 76.74 percent,
H = 6.97 -
gefunden:found:
C = 76,63 Prozent,
H = 7,i3 - ·C = 76.63 percent,
H = 7, i3 - ·
Die neuen ου-Aminoalkylchinoline sollen in der Therapie und als Ausgangsstoffe für die Herstellung anderer pharmazeutischer Produkte Verwendung finden.The new ου-aminoalkylquinolines are said to be in the Therapy and as starting materials for the manufacture of other pharmaceutical products Find use.
Claims (1)
Methoden reduziert.(Ri and Rh as above)
Methods reduced.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE285637C true DE285637C (en) |
Family
ID=541013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT285637D Active DE285637C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE285637C (en) |
-
0
- DE DENDAT285637D patent/DE285637C/de active Active
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