Ethyl bromoacetate → HCID 54292818, compound

HRID 1075673Notes

Reaction equation

HRID 1075673 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:19]=[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]2=[O:29])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([O:32][C:33](=[O:36])[CH2:34]Br)[CH3:31].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:30]([O:32][C:33](=[O:36])[CH2:34][N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[CH:19][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[C:21]1=[O:29])[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 53974055HCID 53974055, compound

Product 1

HCID 54292818HCID 54292818, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(8-benzyloxyquinol-5-ylmethylen)-2-oxindole (140 mg, 0.37 mmol) in acetone (10 ml) was added 2-bromoacetic acid ethyl ester (151 mg, 0.9 mmol) and anhydrous potassium carbonate (150 mg) and the reaction mixture was stirred for 8 h at 50° C. Then the mixture was concentrated under vacuum, the residue taken up with dichloromethane, the organic phase washed several times with water, dried and evaporated. The residue was crystallized from ethyl acetate to give 150 mg (87% yield) of title compound.

Workup

  1. concentrationThen the mixture was concentrated under vacuum
  2. washthe organic phase washed several times with water
  3. customdried
  4. customevaporated
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-58206dc48eed4f58940c6935202111c8
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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