Sodium Chloride → 1,2,3,4-Tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7](C(OC)=O)[CH:6]2[CH2:18][C:19]([O:21][CH3:22])=[O:20].[Cl-].[Na+]>O.CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH:6]2[CH2:18][C:19]([O:21][CH3:22])=[O:20]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 155 °C
Procedure
A mixture of 67.0 g of 1,2,3,4-tetrahydro-6-methoxy-3-(methoxycarbonyl)-2-oxo-4-quinoline acetic acid, methyl ester and 13 g of sodium chloride in 23 ml of water and 300 ml of dimethyl sulfoxide was heated at 155° C. for 6 hours, cooled, and diluted with 1.2 l of a 1:1 mixture of ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate, and the combined organic layers were washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 1,2,3,4-tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester.
Workup
- temperaturecooled
- customThe aqueous phase was separated
- extractionextracted with ethyl acetate
- washthe combined organic layers were washed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-551a29a8b74f4ebcaed26caca6c17f0e
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05097033
Reaction notes
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