Sodium Chloride → 1,2,3,4-Tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester

HRID 1085420Notes

Reaction equation

HRID 1085420 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

HCID 5234Sodium ChlorideHCID 156788681,2,3,4-Tetrahydro-6-methoxy-3-(methoxycarbonyl)-2-oxo-4-quinoline acetic acid, methyl ester

Product 1

HCID 156788691,2,3,4-Tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

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

  1. temperaturecooled
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. washthe combined organic layers were washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbe3e79d30044d9fa0f0e7d411957da5
Source dataset
uspto-grants-1991_04
Patent number
US05010083

Reaction notes

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