Ethyl bromoacetate → 2-(5-Formylquinol-8-yloxy)acetic acid ethyl ester

HRID 1075669Notes

Reaction equation

HRID 1075669 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21]>CN(C=O)C.ClCCl>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[O:13])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:21]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2753638-Hydroxyquinoline-5-carbaldehyde

Product 1

HCID 541785432-(5-Formylquinol-8-yloxy)acetic acid ethyl esterYield 74.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-hydroxyquinoline-5-carbaldehyde (170 mg, 0.98 mmol) in DMF (5 ml) were added anhydrous potassium carbonate (150 mg) and 2-bromoacetic acid ethyl ester (0.12 ml, 180 mg, 1.08 mmol) at room temperature and the stirring was continued for 1 h. Then the reaction mixture was diluted with dichloromethane, the organic layer was washed several times with water, dried over sodium sulfate and then evaporated under vacuum. The residue was chromatographed on silica gel with ethyl acetate/cyclohexane (9:1) as eluant; to give 190 mg (74.8% yield) of pure 2-(5-formylquinol-8-yloxy)acetic acid ethyl ester.

Workup

  1. washthe organic layer was washed several times with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated under vacuum
  4. customThe residue was chromatographed on silica gel with ethyl acetate/cyclohexane (9:1) as eluant

Sources & evidence

ORD record
ord-84a67448d5a3482ea2c4dbbb2a16a053
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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