1-Bromohexane → 1-hexyl-5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone

HRID 1033525Notes

Reaction equation

HRID 1033525 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+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH2:16]([N:7]1[C:8]2[CH2:9][CH2:10][CH2:11][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5][C:6]1=[O:12])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 62714Lithium hydrideHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

Product 1

HCID 104220861-hexyl-5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone (10.0 g), lithium hydride (0.78 g), and dimethylformamide (400 ml) was stirred for 3 hrs at 25° C., under nitrogen. 1-Bromohexane (10.6 g) was added and the mxture 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 separted 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 purified by high performance liquid chromatography (silica gel, two columns, eluted with 50% ethyl acetate/hexane). The appropriate fractions were collected and evaporated to give 4.6 (31%) of 1-hexyl-5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone.

Workup

  1. stirringthe mxture was stirred for an additional eighteen hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by high performance liquid chromatography (silica gel, two columns, eluted with 50% ethyl acetate/hexane)
  10. customThe appropriate fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-173e46cad03441a885fb29a593921069
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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