Phenethyl bromide → 5,6,7,8-tetrahydro-5-oxo-1-(2-phenylethyl)-2(1H)-quinolinone

HRID 1033526Notes

Reaction equation

HRID 1033526 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:7][C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2.[H-].[Li+].[C:15]1([CH2:21][CH2:22]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]([CH2:22][CH2:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 62714Lithium hydrideHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

Product 1

HCID 103556185,6,7,8-tetrahydro-5-oxo-1-(2-phenylethyl)-2(1H)-quinolinoneYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone (7.5 g), lithium hydride (0.59 g), and dimethylformamide (300 ml) was stirred for 3 hrs at 25° C., under nitrogen. 2-Phenylethyl bromide (9.36 g) was added and the mixture was stirred for an additional eighteen hrs. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with petroleum ether to afford 3.0 g (24%) of 5,6,7,8-tetrahydro-5-oxo-1-(2-phenylethyl)-2(1H)-quinolinone.

Workup

  1. stirringthe mixture was stirred for an additional eighteen hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-5dbdf1db47a643e593e5011058664b8e
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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