Potassium Carbonate → 3-chloro-1-(4-methoxy-benzyl)-5-nitro-1H-pyridin-2-one

HRID 2410129Notes

Reaction equation

HRID 2410129 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[Cl:11][C:12]1[C:13]([OH:21])=[N:14][CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:11][C:12]1[C:13](=[O:21])[N:14]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 178526838HCID 178526838, compound

Product 1

HCID 867031253-chloro-1-(4-methoxy-benzyl)-5-nitro-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methoxybenzyl bromide (5.0 mL, 34.4 mmol) was added to a cold (0° C.) mixture 3-chloro-2-hydroxy-5-nitropyridine (5 g, 28.6 mmol) and K2CO3 (7.9 g, 57.3 mmol) in DMF (25 mL). The reaction mixture was allowed to warm to rt, stirred for 2 h, quenched by addition of a saturated aqueous NaHCO3 solution, and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by trituration in EtOAc. tR: 0.98 min (LC-MS 2); ESI-MS: 295.2 [M+H]+ (LC-MS 2).

Workup

  1. customquenched by addition of a saturated aqueous NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by trituration in EtOAc

Sources & evidence

ORD record
ord-773b68ea8aee492098f913e596442f85
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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