US4656283A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid
Assignee: Wyeth Holdings LLC
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Filing: 1985-02-04
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Granted: 1987-04-07
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Expires: 2005-02-04
Abstract
Abstract There are provided novel alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid; novel dialkyl 3-(substituted)phenylaminobut-2-ene-dioates, useful as intermediates for the preparation of highly effective 2-(2-imidazolin-2-yl)quinoline herbicidal agents and methods for the preparation thereof.
Inventors
- 👤 Robert F. Doehner, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:41
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A01; A01N; A01N43/00; A01N43/48; A01N43/50; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
212 words
A method for the preparation of a compound having the structure: ##STR22## wherein R' is CH 3 or COOR"; R" is C 1 -C 4 alkyl; L, M, Q and R 7 are each H, halogen (Cl, Br, F or I); C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, halo(C 1 -C 4 )alkyl, NO 2 , CN, phenyl, phenoxy, difluoromethoxy, loweralkylamino, chlorophenyl or phenoxy substituted with one Cl, CF 3 , NO 2 or CH 3 group, with the proviso that only one of L, M, Q or R 7 , may represent a substituent other than hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy; comprising, reacting a compound having the structure: ##STR23## wherein L, M, Q, R 7 , R' and R" are as described above, with an approximately equimolar amount of an immonium salt having the structure: Cl--CH═N.sup.⊕ --(R"').sub.2.a where R"' is C 1 -C 4 alkyl or when taken jointly with the nitrogen forms a 5 or 6 member ring and a is PO 2 Cl 2 .sup.⊖ or Cl.sup.⊖ in the presence of a hydrocarbon solvent, a chlorinated hydrocarbon solvent, or mixtures thereof at a temperature between 40° to 110° C.
Claim 2
Independent Claim
212 words
A method for the preparation of a compound having the structure: ##STR22## wherein R' is CH 3 or COOR"; R" is C 1 -C 4 alkyl; L, M, Q and R 7 are each H, halogen (Cl, Br, F or I); C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, halo(C 1 -C 4 )alkyl, NO 2 , CN, phenyl, phenoxy, difluoromethoxy, loweralkylamino, chlorophenyl or phenoxy substituted with one Cl, CF 3 , NO 2 or CH 3 group, with the proviso that only one of L, M, Q or R 7 , may represent a substituent other than hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy; comprising, reacting a compound having the structure: ##STR23## wherein L, M, Q, R 7 , R' and R" are as described above, with an approximately equimolar amount of an immonium salt having the structure: Cl--CH═N.sup.⊕ --(R"').sub.2.a where R"' is C 1 -C 4 alkyl or when taken jointly with the nitrogen forms a 5 or 6 member ring and a is PO 2 Cl 2 .sup.⊖ or Cl.sup.⊖ in the presence of a hydrocarbon solvent, a chlorinated hydrocarbon solvent, or mixtures thereof at a temperature between 40° to 110° C.
Claim 3
Dependent Claim
35 words
A method according to claim 1 wherein the chlorinated hydrocarbon solvent is methylene chloride, or dichlorethane, chlorobenzene, orthodichlorobenzene and the reaction mixture is heated for a period of time sufficient to essentially complete the reaction.
Claim 4
Dependent Claim
18 words
A method according to claim 2 wherein R' is COOR" and R" is C 1 -C 4 alkyl.
Claim 5
Dependent Claim
19 words
A method according to claim 2 wherein R' is CH 3 and R" is C 1 -C 4 alkyl.
Claim 6
Dependent Claim
55 words
A method according to claim 1 with the addition step of preparing the immonium reactant in situ comprising, admixing, in the presence of a solvent, equimolar amounts of dimethylformamide and a compound POCl 3 , COCl 2 , ClCOCOCl or SOCl 2 and the compound having the structure ##STR24## is added to the reaction mixture.
Claim 7
Dependent Claim
31 words
A method according to claim 5 wherein the hydrocarbon solvent is toluene and the reaction mixture is heated at reflux for a period of time sufficient to essentially complete the reaction.
References Cited (Backward Citations)
No citation records indexed.
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| 3.5 Years (Year 4) | 1990-04-06 | 1990-10-06 | 1991-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-06 | 1994-10-06 | 1995-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-06 | 1998-10-06 | 1999-04-07 | $7700.00 | Window Closed / Lapsed |