Dimethylformamide → HCID 19603497, compound

HRID 1604580Notes

Reaction equation

HRID 1604580 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:34](I)[CH3:35]>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[C:20]([O:22][CH2:34][CH3:35])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 19603439HCID 19603439, compound

Product 1

HCID 19603497HCID 19603497, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 8-benzyloxy-4-carboxy-2-methylquinoline (700 mg), potassium carbonate (659 mg) and N,N-dimethylformamide (0.3 ml) was dropwise added ethyl iodide (409 mg) under ice-cooling and the mixture was stirred for 30 minutes at the same temperature and for 1 hour at ambient temperature. To the mixture was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, dried over magnesium sulfate. The solvent was removed, and the residue was crystallized from diisopropyl ether to give 8-benzyloxy-4-ethoxycarbonyl-2-methylquinoline (686 mg) as solid.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed
  7. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-02637fbec46c4bafa439154ae5d90e17
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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