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

HRID 1195179Notes

Reaction equation

HRID 1195179 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 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 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 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 purified by high performance liquid chromatography (silica gel, two columns, eluted with 50% ethyl acetate/hexane)
  11. customThe appropriate fractions were collected
  12. customevaporated

Sources & evidence

ORD record
ord-b1ef8c083bc0479ca1e2b3492c030d95
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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