Water → Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-isopropoxyquinoline-3-carboxylate

HRID 862628Notes

Reaction equation

HRID 862628 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[NH:11][C:10](=[O:17])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]2[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1.Br[CH:34]([CH3:36])[CH3:35].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([O:17][CH:34]([CH3:36])[CH3:35])[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]2[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 22097611ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate

Product 1

HCID 22097610Ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-isopropoxyquinoline-3-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oily sodium hydride (60%, 0.1 g) was added to a solution of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2(1H)-quinolone-3-carboxylate (0.5 g) in N,N-dimethylformamide (20 ml) under ice-cooling. After stirring at room temperature for 30 minutes, 2-bromopropane (0.5 ml) was added. The mixture was stirred at 60° C. for 5 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-isopropoxyquinoline-3-carboxylate (0.388 g, 70%) which was then recrystallized from ethyl ether. mp. 142°-143° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 60° C. for 5 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-48970444666942759a3728e4c87fcfa1
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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