Process of preparing diaminopyridine compounds

Details Process of preparing diaminopyridine compounds Process of preparing diaminopyridine compounds

1994-06-17

1996-07-16

Davis, Zinna Northington

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

5462821, 5462834, C07D21384, C07D21385, C07D40512

Patent

active

055368409

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/00538, filed Mar. 10, 1993.
The present invention relates to a novel process for preparing 2,6-diaminocyanopyridines by reacting the 2,6-dichloro compounds with amines.
U.S. Pat. No. 3,853,895 discloses the preparation of 2,6-diaminopyridines. However, the manner of preparation described therein is unsatisfactory, since large amounts of amine are required and, what is more, the target products are obtained only in a low yield.
Furthermore, DE-A-2 260 827, DE-A-2 916 319 and U.S. application Ser. No. 3,980,659 describe the preparation of 2,6-diaminocyanopyridines using the corresponding dichloro or aminomonochloro compounds as starting materials.
It is an object of the present invention to provide a novel process for preparing 2,6-diaminocyanopyridines which likewise starts from the 2,6-dichloro compounds and gives the target products in a simple manner and in high yield and purity.
We have found that this object is achieved in an advantageous manner by a process for preparing diaminopyridines of the formula I ##STR3## where
one of the two radicals X.sup.1 and X.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or nitro and the other is cyano,
R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,
R.sup.2 and R.sup.3 are each independently of one another hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and
R.sup.5 is C.sub.1 -C.sub.10 -alkyl which may be interrupted by from 1 to 3 oxygen atoms in ether function and is optionally hydroxyl-, C.sub.1 -C.sub.4 -alkanoyloxy-, phenoxy-, phenyl-, tetrahydrofuranyl- or tetrahydropyranyl-substituted, C.sub.3 -C.sub.4 -alkenyl or C.sub.5 -C.sub.7 -cycloalkyl, ##STR4## where R.sup.1 and X.sup.1 are each as defined above, with amines by reacting in a first step a dichloropyridine of the formula II with an amine of the formula III the presence of a base and of an inert organic diluent and/or water, then removing the diluent and thereafter, with or without prior intermediate isolation of the reaction product, reacting it in a second step with an aniline of the formula IV ##STR5## where R.sup.2, R.sup.3 and R.sup.4 are each as defined above, which comprises carrying out the second step in a melt at from 90.degree. to 165.degree. C. and at a pH from 3.5 to 6.5 using 1.3 to 3 mol of aniline IV per mole of dichloropyridine II.
Any alkyl appearing in the abovementioned formulae may be not only straight-chain but also branched.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X.sup.1 and X.sup.2 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
R.sup.4 may also be for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
R.sup.5 may also be for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, benzyl, 1- or 2-phenylethyl, 2- or 3-phenylpropyl, 3-phenylprop-2-yl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3- hydroxyprop-2-yl, 2-hydroxybutyl, 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonly, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 4,8,12-trioxatridecyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 2-phenoxybutyl, 4-phenoxybutyl, 5-phenoxypentyl, 6-phenoxyhexyl, 5-hydroxy-3-oxapentyl, 8-hydroxy-4-oxaoctyl, 6 -phenoxy-4-oxahexyl, 2-formyloxyethyl, 2-acetyloxyethyl, 2-propionyloxyethyl, 2- or 3-formyloxypropyl, 2- or 3-acetyloxypropyl, 2- or 3-propionyloxypropyl, 2- or 4-formyloxybutyl, 2- or 4-acetyloxybutyl, 2- or 4-propionyloxybutyl, 2-(tetrahydropyran-4-yl)ethyl, 2- or 3-(tetrahydropyran-4-yl)-propyl, 2- or 4-(tetrahydropyran-4-yl)butyl, prop-2-en

REFERENCES:
patent: 3853895 (1974-12-01), Lamm et al.
patent: 3980659 (1976-09-01), Fleckenstein et al.
patent: 4325870 (1982-04-01), Buhler et al.

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