US4459408A
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US
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Process for the preparation of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinoline-carboxylic acid and alkyl 2-trichloromethyl-3-quinoline-carboxylate intermediates therefor
Assignee: Wyeth Holdings LLC
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Filing: 1982-05-25
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Granted: 1984-07-10
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Expires: 2002-05-25
Abstract
Abstract The invention is related to a novel process for the prepartion of 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid, a useful and valuable herbicide.
Inventors
- 👤 Donald R. Maulding
- 👤 Robert F. Doehner, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:14
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
135 words
A process for the preparation of a compound of formula ##STR4## comprising reacting one molar equivalent of a compound of formula ##STR5## wherein R is C 1 -C 3 alkyl with from one molar equivalent to two molar equivalents of 2-amino-2,3-dimethylbutyramide; in the presence of an inert solvent of benzene, toluene or xylene; and from 3 molar equivalents to 5 molar equivalents of anhydrous sodium or potassium hydroxide; 2 molar equivalents of anhydrous sodium or potassium carbonate, and from 0.1 molar equivalent to 0.3 molar equivalent of a phase transfer catalyst of tetra(C 3 -C 6 )alkylammonium salts, benzyltri(C 1 -C 6 )alkylammonium salts, crown ethers or tetraalkylphosphonium salts; from 80° C. to 130° C. or at the atmospheric boiling point of the solvent for a period of time sufficient to essentially complete the reaction.
Claim 2
Dependent Claim
135 words
A process for the preparation of a compound of formula ##STR4## comprising reacting one molar equivalent of a compound of formula ##STR5## wherein R is C 1 -C 3 alkyl with from one molar equivalent to two molar equivalents of 2-amino-2,3-dimethylbutyramide; in the presence of an inert solvent of benzene, toluene or xylene; and from 3 molar equivalents to 5 molar equivalents of anhydrous sodium or potassium hydroxide; 2 molar equivalents of anhydrous sodium or potassium carbonate, and from 0.1 molar equivalent to 0.3 molar equivalent of a phase transfer catalyst of tetra(C 3 -C 6 )alkylammonium salts, benzyltri(C 1 -C 6 )alkylammonium salts, crown ethers or tetraalkylphosphonium salts; from 80° C. to 130° C. or at the atmospheric boiling point of the solvent for a period of time sufficient to essentially complete the reaction.
Claim 3
Dependent Claim
65 words
A process according to claim 1, wherein the amount of 2-amino-2,3-dimethylbutyramide is one molar equivalent; the solvent is toluene; the amount of sodium hydroxide is 3.3 molar equivalents; the amount of potassium carbonate is two molar equivalents; the phase transfer catalyst is tetrabutylammonium hydrogen sulfate used in a 0.1 molar equivalent amount; and the temperature of the reaction is the atmospheric boiling point of toluene.
Claim 4
Dependent Claim
14 words
A compound of the formula: ##STR6## wherein R is C 1 -C 3 alkyl.
Claim 5
Dependent Claim
14 words
A compound of the formula: ##STR6## wherein R is C 1 -C 3 alkyl.
Claim 6
Dependent Claim
8 words
A compound according to claim 3, ethyl 2-trichloromethyl-3-quinolinecarboxylate.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-07-10 | 1988-01-09 | 1988-07-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-10 | 1992-01-09 | 1992-07-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-10 | 1996-01-09 | 1996-07-10 | $7700.00 | Window Closed / Lapsed |