BE859768R - PROCESS FOR THE CATALYTIC PREPARATION OF PYRIDINES SUBSTITUTED IN POSITION 2 - Google Patents
PROCESS FOR THE CATALYTIC PREPARATION OF PYRIDINES SUBSTITUTED IN POSITION 2Info
- Publication number
- BE859768R BE859768R BE181781A BE181781A BE859768R BE 859768 R BE859768 R BE 859768R BE 181781 A BE181781 A BE 181781A BE 181781 A BE181781 A BE 181781A BE 859768 R BE859768 R BE 859768R
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- catalytic preparation
- pyridines substituted
- acetylene
- reaction
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Description
Procédé de préparation catalytique de pyridines
substituées en position 2 <EMI ID=1.1>
partir des dérivés cyano correspondants et d'acétylène et il est caractérisé en ce que l'on réalise la réaction à température élevée en présence de cobaltocène comme catalyseur.
La présente addition concerne un procédé de préparation de
<EMI ID=2.1>
<EMI ID=3.1>
<EMI ID=4.1> 2
lino
<EMI ID=5.1>
<EMI ID=6.1>
<EMI ID=7.1>
<EMI ID=8.1>
R2
plus haut, avec de l'acétylène en présence de ccbaltocène comme
<EMI ID=9.1>
dans le fait que l'on peut appliquer avec ce catalyseur des températures supérieures à 80[deg.]C. De la sorte, il est possible de
<EMI ID=10.1>
<EMI ID=11.1>
de l'acétylène avec lui-même pour former du benzène et des polymères.
<EMI ID=12.1>
cyanamides de façon connue à partir du chlorure de cyanogène
et des amines secondaires correspondantes comme décrit par exemple dans le brevet BE n[deg.] 641 601.
Pour mettre en oeuvre le procédé selon l'invention, on sature les composés du cyanamide correspondant et le cobaltocène par de l'acétylène dans un récipient sous pression et on chauffe.
On réalise de préférence la réaction sous 10 à 25 bars et
<EMI ID=13.1>
<EMI ID=14.1>
<EMI ID=15.1>
<EMI ID=16.1>
sives ou bien réalimenté en continu.
Par le choix de la quantité de catalyseur, de la pression et de la température dans les limites indiquées on peut transformer plus de 20 moles de composé cyano par mole de catalyseur et par heure.
<EMI ID=17.1>
cyano qui n'a pas réagi, et éventuellement un mélange avec du benzène.
Pour la mise en oeuvre de la réaction, il n'est normalement pas nécessaire d'avoir recours à un solvant, mais toutefois on
<EMI ID=18.1>
<EMI ID=19.1>
la préparation comme agents de dilution.
<EMI ID=20.1>
par exemple dans un tube à écoulement;,
Les exemples suivants, non limitatifs, servent à illustrer l'invention.
EXEMPLE 1.
<EMI ID=21.1>
dans 44,0 g de benzène, on ajoute 164 g de N,N-diméthylcyanamide <EMI ID=22.1> <EMI ID=23.1>
et on augmente doucement le chauffage de telle sorte que dans
<EMI ID=24.1>
pression dans l'autoclave jusqu'à une valeur inférieure à
12 atmosphères on rajoute de l'acétylène sous pression. Après
10 heures de réaction on refroidit et on détend. On obtient par distillation fractionnée après le benzène et des petites
<EMI ID=25.1>
<EMI ID=26.1>
<EMI ID=27.1>
EXEMPLE 3.
De façon analogue à celle de l'exemple 1, on traite 2,0 g
<EMI ID=28.1>
<EMI ID=29.1>
<EMI ID=30.1>
<EMI ID=31.1>
<EMI ID=32.1>
<EMI ID=33.1>
tuées de formule générale
<EMI ID=34.1>
<EMI ID=35.1>
rents, représentent un groupe alcoyle, cycloalcoyle ou aryle ou
bien,
<EMI ID=36.1>
<EMI ID=37.1>
<EMI ID=38.1>
<EMI ID=39.1>
<EMI ID=40.1>
plus haut avec de l'acétylène en présence .de cobaltocène comme catalyseur à des températures et des pressions élevées.
Process for the catalytic preparation of pyridines
substituted in position 2 <EMI ID = 1.1>
starting from the corresponding cyano derivatives and acetylene and it is characterized in that the reaction is carried out at high temperature in the presence of cobaltocene as catalyst.
The present addition relates to a process for preparing
<EMI ID = 2.1>
<EMI ID = 3.1>
<EMI ID = 4.1> 2
lino
<EMI ID = 5.1>
<EMI ID = 6.1>
<EMI ID = 7.1>
<EMI ID = 8.1>
R2
above, with acetylene in the presence of ccbaltocene as
<EMI ID = 9.1>
in the fact that one can apply with this catalyst temperatures higher than 80 [deg.] C. In this way, it is possible to
<EMI ID = 10.1>
<EMI ID = 11.1>
acetylene with itself to form benzene and polymers.
<EMI ID = 12.1>
cyanamides in a known manner from cyanogen chloride
and corresponding secondary amines as described, for example, in BE patent no. [deg.] 641,601.
To carry out the process according to the invention, the compounds of the corresponding cyanamide and the cobaltocene are saturated with acetylene in a pressure vessel and the mixture is heated.
The reaction is preferably carried out at 10 to 25 bars and
<EMI ID = 13.1>
<EMI ID = 14.1>
<EMI ID = 15.1>
<EMI ID = 16.1>
sives or continuously replenished.
By choosing the amount of catalyst, the pressure and the temperature within the limits indicated, it is possible to convert more than 20 moles of cyano compound per mole of catalyst and per hour.
<EMI ID = 17.1>
cyano which has not reacted, and possibly a mixture with benzene.
In order to carry out the reaction, it is normally not necessary to resort to a solvent, but nevertheless one
<EMI ID = 18.1>
<EMI ID = 19.1>
the preparation as diluting agents.
<EMI ID = 20.1>
for example in a flow tube ;,
The following non-limiting examples serve to illustrate the invention.
EXAMPLE 1.
<EMI ID = 21.1>
164 g of N, N-dimethylcyanamide are added to 44.0 g of benzene <EMI ID = 22.1> <EMI ID = 23.1>
and the heating is slowly increased so that in
<EMI ID = 24.1>
pressure in the autoclave to a value less than
12 atmospheres, acetylene is added under pressure. After
10 hours of reaction, cooled and relaxed. Is obtained by fractional distillation after benzene and small
<EMI ID = 25.1>
<EMI ID = 26.1>
<EMI ID = 27.1>
EXAMPLE 3.
In a manner analogous to that of Example 1, 2.0 g are treated
<EMI ID = 28.1>
<EMI ID = 29.1>
<EMI ID = 30.1>
<EMI ID = 31.1>
<EMI ID = 32.1>
<EMI ID = 33.1>
general formula killed
<EMI ID = 34.1>
<EMI ID = 35.1>
rents, represent an alkyl, cycloalkyl or aryl group or
well,
<EMI ID = 36.1>
<EMI ID = 37.1>
<EMI ID = 38.1>
<EMI ID = 39.1>
<EMI ID = 40.1>
above with acetylene in the presence of cobaltocene as a catalyst at elevated temperatures and pressures.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH947177A CH630357A5 (en) | 1977-08-02 | 1977-08-02 | Process for the preparation of 2-N,N-disubstituted aminopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE859768R true BE859768R (en) | 1978-04-14 |
Family
ID=4352339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE181781A BE859768R (en) | 1977-08-02 | 1977-10-14 | PROCESS FOR THE CATALYTIC PREPARATION OF PYRIDINES SUBSTITUTED IN POSITION 2 |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE859768R (en) |
| CH (1) | CH630357A5 (en) |
-
1977
- 1977-08-02 CH CH947177A patent/CH630357A5/en not_active IP Right Cessation
- 1977-10-14 BE BE181781A patent/BE859768R/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH630357A5 (en) | 1982-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: LONZA S.A. Effective date: 19880930 |