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

HRID 2410129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410129
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-773b68ea8aee492098f913e596442f85
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815926B2

Notizen zur Reaktion

Wird geladen…