Ethyl bromoacetate → Ethyl 2-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetate

HRID 1023153Notes

Reaction equation

HRID 1023153 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[O:12]=[C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:3]=2)[NH:8]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 12821879Ethyl 2-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetateYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (2.5 g, 15.3 mmol) in dry DMF (10 ml) was added potassium carbonate (4.2 g, 30.3 mmol) and ethyl bromoacetate (2.4 g, 14.3 mmol). The reaction was stirred at room temperature for 2 h. Completion of the reaction was monitored by TLC. Solvent was removed under vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with water (20 mL), brine (20 mL), and dried over sodium sulfate. The organic layer was concentrated under vacuum to afford 2.7 g of crude material which was purified by silica gel flash chromatography (24 g, 2% methanol in chloroform) to afford 2.8 g (73%) of ethyl 2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetate as a white solid. 1H NMR: 400 MHz, DMSO-d6: δ 1.21 (t, J=7.20 Hz, 3H), 2.40 (t, J=7.20 Hz, 2H), 2.83 (t, J=8.00 Hz, 2H), 4.17 (q, J=7.20 Hz, 2H), 4.69 (s, 2H), 6.71-6.80 (m, 3H), 9.92 (s, 1H). LCMS: RT 1.31 min. LCMS (ES-API), m/z 250.0 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with water (20 mL), brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated under vacuum
  6. customto afford 2.7 g of crude material which
  7. customwas purified by silica gel flash chromatography (24 g, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-2e6f0359277c4f7e876edd37fdd482d0
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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