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Process for the preparation of dialkyl pyridine-2,3-dicarboxylate and derivatives thereof from dialkyl dichlorosuccinate

Assignee: BASF SE
•
Filing: 1990-06-15
•
Granted: 1992-06-23
•
Expires: 2010-06-15
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Abstract

Abstract There is provided a process for the preparation of substituted and unsubstituted-2,3-pyridinedicarboxylate compounds by reacting a dialkyl dichlorosuccinate with a dehydrohalogenating agent, an ammonia source and an appropriately substituted α,β-unsaturated aldehyde or ketone.

Inventors

  • 👤 Albert A. Cevasco
  • 👤 George A. Chiarello
  • 👤 William F. Rieker

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 06:10
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 177 words
A process for the preparation of a compound of formula I ##STR5## wherein R is C 1 -C 6 alkyl; X and Z are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 5 alkenyl and Y is hydrogen, halogen, C 1 -C 6 alkyl optionally substituted with one to three halogens, hydroxy groups, C 1 14 C 4 alkoxy groups or C 1 -C 4 alkylthio groups, C 1 -C 4 alkoxycarbonyl, aminocarbonyl, phenylthio, substituted phenylthio, phenoxy, substituted phenoxy, phenyl or substituted phenyl which comprises reacting a dialkyl dichlorosuccinate of formula II ##STR6## wherein R is C 1 -C 6 alkyl with a dehydrohalogenating agent in the presence of a solvent to form a first intermediate, reacting said first intermediate with an ammonia source to form a second intermediate, reacting said second intermediate with an α, β-unsaturated aldehyde or ketone of formula III ##STR7## wherein X, Y and Z are described above and an acid in the presence of the solvent, to form the formula I pyridinedicarboxylate compound.
Claim 2
Dependent Claim 177 words
A process for the preparation of a compound of formula I ##STR5## wherein R is C 1 -C 6 alkyl; X and Z are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 5 alkenyl and Y is hydrogen, halogen, C 1 -C 6 alkyl optionally substituted with one to three halogens, hydroxy groups, C 1 14 C 4 alkoxy groups or C 1 -C 4 alkylthio groups, C 1 -C 4 alkoxycarbonyl, aminocarbonyl, phenylthio, substituted phenylthio, phenoxy, substituted phenoxy, phenyl or substituted phenyl which comprises reacting a dialkyl dichlorosuccinate of formula II ##STR6## wherein R is C 1 -C 6 alkyl with a dehydrohalogenating agent in the presence of a solvent to form a first intermediate, reacting said first intermediate with an ammonia source to form a second intermediate, reacting said second intermediate with an α, β-unsaturated aldehyde or ketone of formula III ##STR7## wherein X, Y and Z are described above and an acid in the presence of the solvent, to form the formula I pyridinedicarboxylate compound.
Claim 3
Dependent Claim 52 words
The process according to claim 1 for the preparation of the formula I pyridinedicarboxylate compound wherein X and Z are hydrogen and Y is hydrogen, halogen or C 1 -C 4 alkyl optionally substituted with one to three halogens, C 1 -C 4 alkoxy groups or C 1 -C 4 alkylthio groups.
Claim 4
Dependent Claim 26 words
The process according to claim 1 wherein the dehydrohalogenating agent is an ammonium salt, the solvent is a polar solvent and the acid is acetic acid.
Claim 5
Dependent Claim 21 words
The process according to claim 1 wherein the second intermediate is formed at a temperature of about 45° C. or greater.
Claim 6
Dependent Claim 23 words
The process according to claim 1 wherein the formula I pyridinedicarboxylate compound is formed at a temperature of about 45° C. or greater.
Claim 7
Dependent Claim 26 words
The process according to claim 1 wherein the α,β-unsaturated aldehyde or ketone of formula III is present in the amount of at least one molar equivalent.
Claim 8
Dependent Claim 15 words
The process according to claim 2 wherein the formula I compound prepared is dialkyl pyridine-2,3-dicarboxylate.
Claim 9
Dependent Claim 15 words
The process according to claim 2 wherein the formula I compound prepared is dialkyl 5-methyl-2,3-pyridinedicarboxylate.
Claim 10
Dependent Claim 15 words
The process according to claim 2 wherein the formula I compound prepared is dialkyl 5-ethyl-2,3-pyridinedicarboxylate.
Claim 11
Dependent Claim 15 words
The process according to claim 2 wherein the formula I compound prepared is dialkyl 5-(methoxymethyl)-2,3-pyridinedicarboyxlate.
Claim 12
Dependent Claim 15 words
The process according to claim 2 wherein the formulate I compound prepared is dialkyl 5-(chloromethyl)-2,3-pyridinedicarboxylate.
Claim 13
Dependent Claim 15 words
The process according to claim 7 wherein the formula I compound prepared is diethyl pyridine-2,3-dicarboxylate.
Claim 14
Dependent Claim 15 words
The process according to claim 8 wherein the formula I compound prepared is diethyl 5-methyl-2,3-pyridinedicarboxylate.
Claim 15
Dependent Claim 15 words
The process according to claim 9 wherein the formula I compound prepared is diethyl 5-ethyl-2,3-pyridinedicarboxylate.
Claim 16
Dependent Claim 15 words
The process according to claim 10 wherein the formula I compound prepared is diethyl 5-(methoxymethyl)-2,3-pyridinedicarboxylate.
Claim 17
Dependent Claim 15 words
The process according to claim 11 wherein the formula I compound prepared is diethyl 5-(chloromethyl)-2,3-pyridinedicarboxylate.

References Cited (Backward Citations)

US4798619A Cited
US4723011A Cited
US4758667A Cited
EP0299362A1 Cited
US4871859A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-06-23 1995-12-23 1996-06-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-06-23 1999-12-23 2000-06-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-06-23 2003-12-23 2004-06-23 $7700.00 Window Closed / Lapsed

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