2-Pyridone → 5-(4-Chlorophenyl)-1-(2-pentyn-1-yl)-2-pyridinone

HRID 1507

Reaction equation

HRID 1507 reaction equation
[H-].[Na+].[NH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[O:9].Br[CH2:11][C:12]#[C:13][CH2:14][CH3:15].[Cl-:16].[NH4+].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(OCC)(=O)C>CN(C=O)C>[Cl:16][C:20]1[CH:19]=[CH:18][C:23]([C:7]2[CH:6]=[CH:5][C:4](=[O:9])[N:3]([CH2:11][C:12]#[C:13][CH2:14][CH3:15])[CH:8]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 88712-PyridoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 853991-Bromopent-2-yneHCID 21226206Ethyl acetate hexane

Product 1

HCID 189171435-(4-Chlorophenyl)-1-(2-pentyn-1-yl)-2-pyridinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% in mineral oil, 200 mg) in dry DMF (50 ml) at 0° C. was added the preceding pyridinone and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne dropwise. The resulting mixture was kept at 0° C. during one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml) and the combined ether layers washed with brine and dried, yielding the crude product. After column chromatography (silica gel, hexane:ethyl acetate 8:2) the product was obtained as a white amorphous solid.

Workup

  1. waitThe resulting mixture was kept at 0° C. during 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-c9ccf1c64cef45c9a38e8ebb2cfb10e4
Source dataset
uspto-grants-1998_03
Patent number
US05726162

Linked notes

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