Benzyl Bromide → HCID 22051193, compound

HRID 1866875Notes

Reaction equation

HRID 1866875 reaction equation
[C:1]([C:4]1[C:5](=[O:19])[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:1]([C:4]1[C:5](=[O:19])[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:7]([CH3:11])=[CH:8][C:9]=1[O:10][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54724196HCID 54724196, compound

Product 1

HCID 22051193HCID 22051193, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-acetyl-1-(2-chlorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.56 g, 2.02 mmol) in DMF (5.0 mL), benzyl bromide (0.3 mL) and potassium carbonate (0.3 g, 2.16 mmol) were added. The mixture was stirred at room temperature for 3 h, and at 65° C. for 1 h under argon atmosphere. The reaction mixture was concentrated in vacuo and the residue was partitioned between 5% citric acid (25 mL) and EtOAc (50.0 mL). The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated to dryness. The resulting residue was purified by silica gel flash chromatography using 50% EtOAc in hexanes to afford the title compound (0.58 g, 75%) as a pale yellow amorphous substance: 1H-NMR (CD3OD) δ: 7.65-7.3 (m, 9H), 6.5 (s, 1H), 5.31 (s, 2H), 2.42 (s, 3H), and 2.01 (s, 3H); ER-MS m/z=368 (MH+); HR-MS m/z calcd C21H19NO3Cl, 368.1060, found 368.1053.

Workup

  1. waitat 65° C. for 1 h under argon atmosphere
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between 5% citric acid (25 mL) and EtOAc (50.0 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c4377a96bdd444998d881b96322d5720
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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