2-Hydroxyquinoline → 5-Chloro-1-(2-pentyn-1-yl)-2-quinolinone

HRID 1577

Reaction equation

HRID 1577 reaction equation
[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]1=[O:13].Br[CH2:15][C:16]#[C:17][CH2:18][CH3:19].[Cl-:20].[NH4+]>CN(C=O)C.CCCCCC>[Cl:20][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH:6]=[CH:5][C:4](=[O:13])[N:3]2[CH2:15][C:16]#[C:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 60382-HydroxyquinolineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 853991-Bromopent-2-yne

Product 1

HCID 189170945-Chloro-1-(2-pentyn-1-yl)-2-quinolinone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid (1 g).

Workup

  1. waitThe resulting mixture was kept at 0° C. for one half hour
  2. extractionThe aqueous suspension was extracted with ether (3×100 ml)
  3. washthe combined ether layers washed with brine
  4. customdried
  5. customyielding the crude product

Sources & evidence

ORD record
ord-bb2d977cc5f147c5ab274afa7d1d2d39
Source dataset
uspto-grants-1998_03
Patent number
US05726176

Linked notes

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