Process for the preparation of 2,3-pyridinedicarboximides

Details Process for the preparation of 2,3-pyridinedicarboximides Process for the preparation of 2,3-pyridinedicarboximides

1998-06-11

2001-11-13

Rotman, Alan L. (Department: 1612)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C564S256000, C564S265000, C558S411000, C558S414000, C558S418000, C558S419000

Reexamination Certificate

active

06316629

ABSTRACT:

BACKGROUND OF THE INVENTION
2,3-Pyridinedicarboximides are useful as intermediates in the preparation of herbicidal 2-(2-imidazolin-2-yl)nicotinic acids, esters and salts. Methods for the preparation of 2,3-pyridinedicarboximides are known in the art (see, e.g., U.S. Pat. No. 4,748,244; U.S. Pat. No. 4,754,033 and EP 308,084-A1). However, the methods described in those patents and patent application are not entirely satisfactory for the commercial manufacture of 2,3-pyridinedicarboximides.
It is, therefore, an object of the present invention to provide an effective and efficient process for the preparation of 2,3-pyridinedicarboximides.
It is also an object of the present invention to provide a compound which is useful in the process of this invention.
These and other objects and features of the present invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention provides an effective and efficient process for the preparation of a 2,3-pyridine-dicarboxamide having the structural formula I
wherein
R is hydrogen, C
1
-C
6
alkyl or C
1
-C
6
alkoxymethyl;
R
1
is hydrogen, C
1
-C
6
alkyl, C(O)R
2
,
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups,
benzyl optionally substituted on the phenyl ring with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups, or
R
2
is C
1
-C
6
alkyl, benzyl or
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups;
R
3
and R
4
are each independently C
1
-C
4
alkyl; and
R
5
is cyano or CONH
2
,
which process comprises reacting an oxime or hydrazone having the structural formula II
wherein
R is as described above;
R
6
is C
1
-C
6
alkyl;
R
7
is OR
8
or NR
9
R
10
,
R
8
is hydrogen, C
1
-C
6
alkyl, C(O)R
11
,
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups, or
benzyl optionally substituted on the phenyl ring with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups;
R
11
is C
1
-C
6
alkyl, OR
12
, NR
12
R
13
, benzyl or
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups;
R
12
and R
13
are each independently hydrogen, C
1
-C
6
alkyl, benzyl or
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups; and
R
9
and R
10
are each independently hydrogen, C
1
-C
6
alkyl, benzyl or
phenyl optionally substituted with any combination of from one to four halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, nitro or cyano groups,
with a maleimide having the structural formula III
wherein R
1
is as described above.
This invention also relates to the formula II oximes described hereinabove.


REFERENCES:
patent: 4748244 (1988-05-01), Waldner et al.
patent: 4754033 (1988-06-01), Waldner
patent: 4798619 (1989-01-01), Los
patent: 5288866 (1994-02-01), Strong
patent: 5334576 (1994-08-01), Doehner, Jr., et al.
patent: 5571774 (1996-11-01), Hamprect et al.
patent: 205 879 (1986-12-01), None
patent: 0 308 084-A1 (1988-08-01), None
patent: 1406507 (1975-09-01), None
Sylvia J. Allcock, et al., Tetrahedron (1991) 47 No. 48.
Adrian Waldner, Helvetica Chimica Acta (1998) 71 No. 2, pp. 486-492 (Chem. Abst. 110:23757f, 1989).

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