Sodium Chloride → 5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

HRID 1828873Notes

Reaction equation

HRID 1828873 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 119838955-Acetyl-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-acetyl-8-hydroxy-2-quinolone (37.7 g, 186 mmol) was added dimethylformamide (200 mL) and potassium carbonate (34.5 g, 250 mmol) followed by benzyl bromide (31.8 g, 186 mmol). The mixture was stirred at room temperature for 2.25 hour and then poured into saturated sodium chloride (3.5 L) at 0° C. and stirred well for 1 hour. The product was collected and dried on a Buchner funnel for 1 hour, and the resulting solids were dissolved in dichloromethane (2 L) and dried over sodium sulfate. The solution was filtered through a pad of Celite and washed with dichloromethane (5×200 mL). The combined filtrate was then concentrated to dryness and the resulting solids were triturated with ether (500 mL) for 2 hours. The product was collected on a Buchner funnel, washed with ether (2×250 mL) and dried under reduced pressure to give 5-acetyl-8-benzyloxy-2(1H)-quinolinone (EE) (44 g) as an off white powder.

Workup

  1. stirringstirred well for 1 hour
  2. customThe product was collected
  3. customdried on a Buchner funnel for 1 hour
  4. dissolutionthe resulting solids were dissolved in dichloromethane (2 L)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered through a pad of Celite
  7. washwashed with dichloromethane (5×200 mL)
  8. concentrationThe combined filtrate was then concentrated to dryness
  9. customthe resulting solids were triturated with ether (500 mL) for 2 hours
  10. customThe product was collected on a Buchner funnel
  11. washwashed with ether (2×250 mL)
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-7ffe9c0254134093b37508b89eba5208
Source dataset
uspto-grants-2006_06
Patent number
US07060712B2

Reaction notes

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