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Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters
| Details |
Inventors: Wepplo, Peter J.;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Jiles; Henry R.
Assistant Examiner: Dentz; Bernard
Attorney, Agent or Firm: Jackson; H. G.
There is provided a process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters useful as intermediates in the manufacture of herbicidally active 2-(2-imidazolin-2-yl)pyridine compounds. |
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DETAILED DESCRIPTION I claim: 1.
A method for the preparation of compounds having the structure: ##STR28## wherein Q is C.
sub.
1 -C.
sub.
4 alkoxy and Z is hydrogen, C.
sub.
1 -C.
sub.
6 alkyl or phenyl optionally substituted with C.
sub.
1 -C.
sub.
4 alkyl, halogen, C.
sub.
1 -C.
sub.
4 alkoxy, nitro or C.
sub.
1 -C.
sub.
4 alkylthio; comprising reacting an acetylenic ketone having the structure: Z--CO--C.
tbd.
CH, wherein Z is as described above, with an equivalent amount of an aminomaleate having the structure: ##STR29## wherein Q is as described above, or an equivalent amount of an aminofumarate having the structure: ##STR30## wherein Q is as described above; in the presence of a polar solvent, optionally under a blanket of inert gas at a temperature between 50.
degree.
C.
and 100.
degree.
C.
2.
A method according to claim 1, wherein Z is C.
sub.
1 -C.
sub.
6 alkyl and Q is methoxy.
3.
A method according to claim 1, wherein the polar solvent is a C.
sub.
1 -C.
sub.
4 alcohol, dimethylformamide or acetonitrile and the inert gas is nitrogen or argon.
4.
A method according to claim 1, wherein Z is phenyl optionally substituted with fluorine, chlorine, bromine, iodine, or C.
sub.
1 -C.
sub.
6 alkyl and Q is methoxy.
5.
A method according to claim 1, wherein the polar solvent is methanol and the inert gas is nitrogen.
6.
A method according to claim 1, wherein Z is hydrogen and Q is methoxy.
Description:
SUMMARY OF THE INVENTION The invention relates to a process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters which are useful as intermediates in the manufacture of the herbicidally effective 2-(2-imidazolin-2-yl)pyridine compounds described in the application for United States Letters Patent of Marinus Los, Ser.
No.
382,041, filed concurrently herewith and incorporated herein by reference.
The process of the invention involves reaction of a formula (I) acetylenic ketone, having the structure: Z--CO--C.
tbd.
CH, wherein Z is hydrogen, C.
sub.
1 -C.
sub.
6 alkyl or phenyl optionally substituted with C
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