Nitrogen → 4,6-Dimethyl-3-bromo-5-benzyl-1h-pyridin-2-one

HRID 353351Notes

Reaction equation

HRID 353351 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:15])[NH:5][C:4](=[O:16])[CH:3]=1.[Br:17]Br.N#N>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:15])[NH:5][C:4](=[O:16])[C:3]=1[Br:17]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24408BromineHCID 220220554,6-Dimethyl-5-benzyl-1H-pyridin-2-one

Product 1

HCID 220220264,6-Dimethyl-3-bromo-5-benzyl-1h-pyridin-2-oneYield 104.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4,6-dimethyl-5-benzyl-1H-pyridin-2-one (2.21 g, 10.4 mmol) in anhydrous acetic acid (10 mL) was added bromine (3.3 g, 1.06 mL, 20.7 mL). It was stirred at room temperature for one hour. Then the reaction vessel was blew N2 to remove bromine and evaporation removed volatiles. The residue was partitioned between CH2Cl2/sat. NaHCO3/saline (100/50/50 mL). The organic layer was dried over Na2SO4 and evaporation gave the brominated compound as a yellow solid (3.17 g, 100%). 1H NMR (CDCl3) δ 2.07 (s, 3H), 2.37 (s, 3H), 3.81 (s, 2H), 7.00-7.40 (m, 5H); MS (CI) m/z 293, 295 (MH+).

Workup

  1. customto remove
  2. custombromine and evaporation
  3. customremoved volatiles
  4. customThe residue was partitioned between CH2Cl2/
  5. dry with materialThe organic layer was dried over Na2SO4 and evaporation

Sources & evidence

ORD record
ord-cea985c2dd294ed9b04afc7692dc0c7f
Source dataset
uspto-grants-2004_06
Patent number
US06750350B2

Reaction notes

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