Dimethylformamide → HCID 10317047, compound

HRID 1588740Notes

Reaction equation

HRID 1588740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[NH:11][C:10](=[O:20])[C:9]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].[C:26](=O)([O-])[O-].[K+].[K+].CN(C=O)C.CI>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[C:10]([O:20][CH3:26])[C:9]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10383595HCID 10383595, compound

Product 1

HCID 10317047HCID 10317047, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-(2-chlorophenyl)-1,2-dihydro-6,8-dimethyl -2-oxo-3-quinolinecarboxylate (0.71 g), potassium carbonate (0.28 g) and DMF (8 ml) was dropwise added methyl iodide (0.15 ml) under stirring, followed by stirring for 15 minutes at room temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) and concentrated to obtain ethyl 4-(2-chlorophenyl)-2-methoxy-6,8-dimethyl-3-quinolinecarboxylate. Yield 90.3% mp 135°-136° C. (from ethanol)

Workup

  1. stirringby stirring for 15 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-126473bad1a54e79907ba27a4a2b6944
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

Loading…