Patent EP0812828A1 successfully refreshed from Google Patents.
EP0812828A1
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Process for the preparation of (5,6-dicarboxy-3-pyridyl) methyl ammonium halides
Assignee: BASF SE
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Filing: 1997-05-29
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Granted: —
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Expires: 2017-05-29
Abstract
Abstract There is provided a process for the preparation of [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halides having the structural formula I The [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halides are useful as intermediates in the preparation of herbicidal 5-(alkoxymethyl)-2-(2-imidazolin-2-yl)nicotinic acids, esters and salts.
Inventors
- 👤 Wen Xue Wu
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-23 15:24
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; C07D213/24; C07D213/36; C07D213/38; C07D213/61; C07D213/84; C07D215/00; C07D215/02; C07D215/12; C07D215/16; C07D215/18; C07D215/20; C07D215/24; C07D215/26; C07D215/32; C07D215/48; C07D233/00; C07D233/54; C07D233/66; C07D233/70; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
235 words
A process for the preparation of a [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halide having the structural formula I wherein R, R 1 and R 2 are each independently C 1 -C 4 alkyl, and when taken together, R and R 1 may form a 5- or 6-membered ring optionally interrupted by O, S or NR 3 ; R 3 is C 1 -C 4 alkyl; X is Cl, Br or I; Z is hydrogen or halogen; and Z 1 is hydrogen, halogen, cyano or nitro, which process comprises oxidizing a substituted (3-quinolylmethyl)ammonium halide having the structural formula II wherein R, R 1 , R 2 , X, Z and Z 1 are as described for formula I above; R 4 , R 5 , R 6 and R 7 are each independently hydrogen, hydroxy, nitro, OC(O)R 8 , halogen, NR 9 R 10 , C 1 -C 4 alkoxy, SO 3 H, SO 2 Cl or SH, with the proviso that one of R 4 , R 5 , R 6 and R 7 is other than hydrogen or halogen; R 8 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl or NR 11 R 12; R 9 , R 10 , R 11 and R 12 are each independently hydrogen, C 1 -C 4 alkyl or phenyl; the N-oxides thereof; and the acid addition salts thereof, with hydrogen peroxide in the presence of aqueous base.
Claim 2
Dependent Claim
70 words
The process according to claim 1 wherein R, R 1 and R 2 are each independently C 1 -C 4 alkyl; X is Cl or Br; Z and Z 1 are hydrogen; at least one of R 4 , R 5 , R 6 and R 7 is hydroxy, nitro or OC(O)R 8 ; and R 8 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy or phenyl.
Claim 3
Dependent Claim
57 words
The process according to claim 2 wherein R, R 1 and R 2 are methyl; X is Br; R 5 , R 6 , R 7 , Z and Z 1 are hydrogen; R 4 is hydroxy, nitro or OC(O)R 8 ; and R 8 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 4
Dependent Claim
30 words
The process according to claim 1 wherein the hydrogen peroxide is present in an amount from about 8 to 60 molar equivalents relative to the formula II substituted (3-quinolylmethyl)ammonium halide.
Claim 5
Dependent Claim
30 words
The process according to claim 1 wherein the aqueous base is present in an amount of at least about one molar equivalent relative to the formula II substituted (3-quinolylmethyl)ammonium halide.
Claim 6
Dependent Claim
22 words
The process according to claim 5 wherein the aqueous base is present in an amount from about 4 to 10 molar equivalents.
Claim 7
Dependent Claim
18 words
The process according to claim 1 wherein the aqueous base is aqueous sodium hydroxide or aqueous potassium hydroxide.
Claim 8
Dependent Claim
36 words
The process according to claim 1 wherein the formula II substituted (3-quinolylmethyl)ammonium halide is oxidized with hydrogen peroxide in the presence of an aqueous base at a temperature range of about 50 °C to 100 °C.
Claim 9
Dependent Claim
16 words
The process according to claim 8 wherein the temperature is about 75 °C to 95 °C.
Claim 10
Dependent Claim
290 words
A process for the preparation of a herbicidal imidazolinone compound having the formula VI wherein Z and Z 1 are as defined in claim 1; A is O or S; R 12 is C 1 -C 4 alkyl optionally substituted with phenyl optionally substituted with one to three C 1 -C 4 alkyl groups or halogen atoms, or phenyl optionally substituted with one to three C 1 -C 4 alkyl groups or halogen atoms; R 13 is C 1 -C 4 alkyl; R 14 is C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or R 13 and R 14 when taken together with the atom to which they are attached, represent a C 3 -C 6 cycloalkyl group optionally substituted with methyl and R 15 is hydrogen, diloweralkylimino, C 1 -C 12 alkyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, halogen, hydroxy, C 3 -C 6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, lower alkylphenyl, lower alkoxyphenyl, nitrophenyl, carboxyl, loweralkoxycarbonyl, cyano or triloweralkylammonium; C 3 -C 12 alkenyl optionally substituted with one of the following groups: C 1 -C 3 alkoxy, phenyl, halogen or loweralkoxycarbonyl or with two C 1 -C 3 alkoxy groups or two halogen groups; C 3 -C 6 cycloalkyl optionally substituted with one or two C 1 -C 3 alkyl groups; or a cation and when R 13 and R 14 represent different substituents, the optical isomers thereof; which process comprises: (a) preparing a compound having the formula I wherein Z, Z 1 , R, R 1 , R 2 and X are defined in Claim 1 by a process as claimed in Claim 1; and (b) converting the compound having formula I into the compound having the formula VI.
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