DE117006C - - Google Patents
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- Publication number
- DE117006C DE117006C DENDAT117006D DE117006DA DE117006C DE 117006 C DE117006 C DE 117006C DE NDAT117006 D DENDAT117006 D DE NDAT117006D DE 117006D A DE117006D A DE 117006DA DE 117006 C DE117006 C DE 117006C
- Authority
- DE
- Germany
- Prior art keywords
- chloronitronaphthalene
- amido
- autoclave
- hours
- heated
- 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.)
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- UYEFXKQQSBRCGB-UHFFFAOYSA-N 2-chloro-1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Cl)C=CC2=C1 UYEFXKQQSBRCGB-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SMAJHKXZBICXLS-UHFFFAOYSA-N 2-nitronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C=CC2=C1 SMAJHKXZBICXLS-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- -1 halogen nitronaphthalenes Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Das Verfahren bezweckt die Darstellung von Ct1 Ct2-AmIdO- und Ct1 c^-Alkylamidonitronaphtalin aus Ct1 a2-Chlornitronaphtalin und beruht auf der Beobachtung,- dafs sich das Chloratom im Ci1 a2-Chlornitronaphtalin durch die Amido- und Alkylamidogruppe ersetzen läfst.The purpose of the process is the preparation of Ct 1 Ct 2 -AmIdO- and Ct 1 c ^ -alkylamidonitronaphthalene from Ct 1 a 2 -chloronitronaphthalene and is based on the observation that the chlorine atom in Ci 1 a 2 -chloronitronaphthalene is divided by the amido and Replace alkylamido group.
Ueber die Reactionsfähigkeit des Halogens in Halogennitronaphtalinen finden sich bis jetzt in der Literatur noch keine Angaben. Nur von fünffach substituirten Naphtalinderivaten haben Merz und Weith (Ber. 15, 2717) im Tetranitrobromnaphtalin das Brom und Cleve (Ber. 23, 957) im Trinitrodichlornaphtalin ein Chloratom durch die Amidogruppe zu ersetzen vermocht.The reactivity of halogen in halogen nitronaphthalenes has been found up to now no information yet in the literature. Only from five times substituted naphthalene derivatives Merz and Weith (Ber. 15, 2717) have bromine and Cleve in tetranitrobromonaphtalin (Ber. 23, 957) to replace a chlorine atom in trinitrodichloronaphthalene with an amido group able.
Bei der Untersuchung der Chlornitronaphtaline, bei denen beide Substituenten in α-Stellung stehen, also die U1 a2-, O1 Ct3- und Ct1 o.^- Verbindungen, ergab sich die überraschende Thatsache, dafs nur im O1 a2-Chlornitronaphtalin das Chlor leicht gegen die Amido- und Alkylamidogruppe austauschbar ist, während das Chlor in den Stellungen Ci1 as und Ci1 ai unter den gleichen Verhältnissen nicht reagirt.In the investigation of the chloronitronaphthalenes in which both substituents are in the α-position, i.e. the U 1 a 2 , O 1 Ct 3 and Ct 1 o ^ compounds, the surprising fact emerged that only in the O 1 a 2 -chloronitronaphthalene, the chlorine can easily be exchanged for the amido and alkylamido groups, while the chlorine in the positions Ci 1 a s and Ci 1 a i does not react under the same conditions.
Die Umsetzung wird zweckmäfsig durch Erhitzen von Ct1 ct2-Chlornitronaphtalin mit Ammoniak oder den betreffenden Alkylaminen unter Druck im Autoklaven ausgeführt, wenn das blofse Kochen nicht ausreicht oder zu lange Zeit in Anspruch nimmt.The reaction is expediently carried out by heating Ct 1 ct 2 -chloronitronaphthalene with ammonia or the relevant alkylamines under pressure in an autoclave if the mere boiling is insufficient or takes too long.
Beispiel I. 10 kg Ct1 a2-Chlornitronaphtalin werden mit 45 1 einer 8 procentigen aikoholischen Ammoniaklösung im Autoklaven 6 Stunden lang auf 150 bis 1700 erhitzt. Beim Verdünnen mit Wasser fällt aus der Reactionsflüssigkeit das gebildete ατ α2- Nitronaphtylamin aus und kann, wenn nöthig, durch Umlösen aus verdünnter Salzsäure oder durch Krystallisiren aus Benzol gereinigt werden.Example I. 10 kg Ct 1 a 2 -Chlornitronaphtalin are heated with 45 1 of a 8 procentigen aikoholischen ammonia solution in an autoclave for 6 hours at 150 to 170 0th When diluted with water, the α τ α 2 -nitronaphthylamine formed precipitates out of the reaction liquid and can, if necessary, be purified by dissolving from dilute hydrochloric acid or by crystallizing it from benzene.
Wendet man an Stelle von alkoholischem Ammoniak wässeriges an, so mufs die Umsetzungstemperatur um ca. 500 erhöht werden.Applying instead of aqueous alcoholic ammonia to be increased so must, the reaction temperature by about 50 0th
■Beispiel II. 10 kg Ct1 a2-Chlornitronaphtalin werden in 50 1 Alkohol gelöst und mit 25 1 einer 33 procentigen Aethylaminlösung im Autoklaven 6 bis 8 Stunden auf i8o° erhitzt. Beim Erkalten scheidet sich das Aethyl-cij a0-nitronaphtylamin in dunkelrotheo, schön blau fluorescirenden Nadeln aus, die bei 176 bis 1770 schmelzen.Example II. 10 kg of Ct 1 a 2 -chloronitronaphthalene are dissolved in 50 liters of alcohol and heated to 180 ° with 25 liters of a 33 percent ethylamine solution in an autoclave for 6 to 8 hours. On cooling, the ethyl-cij a 0 -nitronaphthylamine precipitates in dark red, beautiful blue fluorescing needles which melt at 176 to 177 0.
Beispiel III. 10 kg Chlornitronaphtalin werden in 50 1 Alkohol gelöst und mit 10 kg Benzylamin im Autoklaven auf 1500 8 Stunden lang erhitzt. Das beim Erkalten auskrysfallisirende Benzyl - Ct1 α2 - mtronaphtylamin wird durch Waschen mit Wasser vom salzsauren Benzylamin befreit und zeigt nach dem Umkrystallisiren aus Benzol den Schmelzpunkt 156°.Example III. 10 kg Chlornitronaphtalin are dissolved in 50 1 of alcohol and heated with 10 kg of benzylamine in an autoclave at 150 0 for 8 hours. The benzyl - Ct 1 α 2 - mtronaphthylamine which crystallizes out on cooling is freed from the hydrochloric acid benzylamine by washing with water and has a melting point of 156 ° after recrystallization from benzene.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE117006C true DE117006C (en) |
Family
ID=386307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT117006D Active DE117006C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE117006C (en) |
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0
- DE DENDAT117006D patent/DE117006C/de active Active
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