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

HRID 1023153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023153
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 12821879Ethyl 2-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetateAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2e6f0359277c4f7e876edd37fdd482d0
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722670B2

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