N-bromobutanimide → 5-bromo-4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one

HRID 2101385Notes

Reaction equation

HRID 2101385 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[NH:11][C:10](=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>CN(C=O)C>[Br:23][C:13]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:9][C:10](=[O:15])[NH:11][C:12]=1[CH3:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 574686404-(4-chloro-phenyl)-6-methyl-1H-pyridin-2-one2×

Product 1

HCID 577993945-bromo-4-(4-chlorophenyl)-6-methylpyridin-2(1H)-oneYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one (1.1 g, 5.0 mmol) in DMF (20 mL) was added NBS (1.07 g, 6.0 mmol) in small portions over 15 min. The reaction mixture was stirred at room temperature for 20 min. Analysis by HPLC/MS indicated the starting 4-(4-chlorophenyl)-6-methylpyridin-2(1H)-one was consumed, and about 17% (based on the UV absorption) of the desired product had formed. The reaction mixture was partitioned between water (50 mL) and EtOAc (50 mL). The resulting suspension was filtered, and the collected solid was washed with water, the dried in a vacuum oven at 50° C. for 16 h to afford 250 mg (17%) of the title compound as an off-white solid. HPLC/MS: retention time=3.35 min, [M+H]+=298.2.

Workup

  1. customwas consumed
  2. customabout 17% (based on the UV absorption) of the desired product
  3. customhad formed
  4. customThe reaction mixture was partitioned between water (50 mL) and EtOAc (50 mL)
  5. filtrationThe resulting suspension was filtered
  6. washthe collected solid was washed with water
  7. customthe dried in a vacuum oven at 50° C. for 16 h

Sources & evidence

ORD record
ord-6249999e514940918f671a4cbc0abed7
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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