Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1980-07-01
1983-02-01
Doll, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
260465E, 260508, 562433, 562457, 562458, 549232, C07D22114, C07D31106, C07C10166
Patent
active
043716946
DESCRIPTION:
BRIEF SUMMARY
This invention relates to the production of polycyclic aromatic compounds, and to novel compounds so produced, and especially to such compounds substituted by secondary or tertiary amine, hydroxyl or ether groups. The polycyclic system is preferably a naphthalene ring. Such compounds have various uses, for instance as dyes, especially fluorescent dyes, as pharmaceuticals (for instance as anti-malarials), and as intermediates for either. The polycyclic ring can be an anthraquinone ring, the compounds then being useful as dyes or dye intermediates.
The synthesis of many aromatic secondary or tertiary amines can be rather difficult to carry out in an economic manner. For instance the production of a compound such as 4-n-butylamino N-n-butylnaphthyl-1,8-imide may involve forming 4-bromo naphthalic anhydride and then reacting this with n-butylamine to form the desired compound, but this suffers from the disadvantages that it is a multistage process, it is difficult to make the bromo compound in good yield, and the use of a bromo derivative necessarily incurs considerable expense.
It is known to make some aromatic amino compounds starting from the corresponding aromatic nitro compound but the methods of conversion again are not entirely satisfactory. Thus while primary amino compounds can often be produced simply by catalytic or chemical reduction, if a secondary or other amino compound is required then the primary amino compound has to be subjected to subsequent reaction, such as with an alkyl halide. In theory a secondary amine can be made in a single stage by reacting the nitro compound with ammonia and an aldehyde and hydrogen and a catalyst under pressure but in practice a mixture of secondary and tertiary amines tends to be produced.
Several processes are known for converting certain nitro-anthraquinones to primary amino anthraquinones. Thus certain nitro anthraquinones can be converted to amino anthraquinones by reaction with sodium sulphite but again the synthesis is not very reliable and only forms a primary amino group.
In British Patent Specification No. 1,524,729 several processes of reducing nitro group in nitroanthraquinones to primary amino group are discussed, and in particular a process is described in which a dinitro anthraquinone is converted to a mono-nitro mono-amino anthraquinone by reaction at a temperature of above 60.degree. C. with ammonia in a dipolar aprotic solvent. It is explained in the specification that the reaction temperature is preferably 100.degree. to 130.degree. C. and that the reaction is preferably conducted by bubbling gaseous ammonia into the solution of dinitro anthraquinone until a total amount of ammonia of up to 50% excess based on the stoichiometric amount has been introduced. For instance in Example 1 complete reaction is said to be achieved after 6 or 7 hours at 120.degree. C. In all the examples a mixture of reaction products is obtained in which the main component is the mono-amino mono-nitro compound. This suggests that one of the nitro groups is activated, for the purposes of the reaction, by the other nitro group.
Whatever the mechanism however the process is restricted to starting with dinitro anthraquinone, it introduces only a primary amine group, and always yields a mixture of products that have to be separated by what is, in practice, a difficult separation technique. Accordingly the process is of no assistance to us in our objective of devising a simple synthesis for the successful economic and easy production of polycyclic aromatic secondary or tertiary amines. It is also our objective to produce other polycyclic aromatic compounds, such as those containing hydroxy or alkoxy substituents.
We have now discovered a new process that appears to be conducted by a reaction mechanism different from any mechanism previously described in the literature for polycyclic aromatic compounds and which is applicable for the production of secondary and tertiary amines, alcohols and alkoxides of naphthalene compounds and also of anthraquinone compounds.
The compounds p
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Okazaki et al., "Chemical Abstracts", vol. 51, Abstract No. 8050g.
Wood et al., "J. Chem. Soc.", vol. 3, pp. 3373-3378, (1962).
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Kimura et al. (I), "Chem. Ab.", vol. 62, Ab. No. 27127c, (1965).
Alexiou Michael S.
Brittain Philip I.
Tyman John H. P.
Brent Chemicals International Limited
Doll John
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