Ethyl Acrylate → (E)-ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)acrylate

HRID 1023167Notes

Reaction equation

HRID 1023167 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7](=[O:21])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2](/[CH:30]=[CH:29]/[C:28]([O:32][CH2:33][CH3:34])=[O:31])=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]2=[O:21])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 672720826-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-one

Product 1

HCID 86680408(E)-ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)acrylateYield 80%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-one (1 g, 2.9 mmol) in DMF (10 mL) were added potassium carbonate (1.19 g, 8.69 mmol), n-tert butyl ammonium chloride (0.66 g, 2.9 mmol), ethyl acrylate (1.16 g, 11.6 mmol) and palladium acetate (0.65 g, 2.9 mmol). The reaction mixture was stirred at room temperature for 20 min, then heated to 120° C. overnight. The reaction mixture was concentrated. To this, was added water and extracted with ethyl acetate, and the combined organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give (E)-ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)acrylate as a white solid (0.8 g, 80%).

Workup

  1. temperatureheated to 120° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. additionTo this, was added water
  4. extractionextracted with ethyl acetate
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9947748c208c4f9fadee10da7cc39e03
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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