Chlorosuccinimide → 2'-acetyl-3-chloro-4-((4-methoxybenzyl)oxy)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

HRID 2199520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199520
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH:12][C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:29]N1C(=O)CCC1=O>CC(O)C.ClC(Cl)C(O)=O>[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[C:12]([Cl:29])[C:11]2=[O:27])[C:7]([CH3:28])=[CH:6][N:5]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 866993052'-Acetyl-4-[(4-methoxyphenyl)methoxy]-5',6-dimethyl[1(2H),4'-bipyridin]-2-one

Produkt 1

HCID 866993042'-acetyl-3-chloro-4-((4-methoxybenzyl)oxy)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6597Dichloroacetic AcidKatalysatorHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2′-acetyl-4-((4-methoxybenzyl)oxy)-5′,6-dimethyl-2H-[1,4′-bipyridin]-2-one of part C (689 mg, 1.82 mmol) in 2-propanol (15 mL) was added N-chlorosuccinimide (266 mg, 2.00 mmol) and 3 drops of dichloroacetic acid. The slurry was heated at 60° C. for 3 hours. The solution was cooled using an ice bath and the resulting white solid was collected by vacuum filtration. The filtrate was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The solution was concentrated in vacuo and purified using normal phase chromatography (ethyl acetate/heptane) and the desired product was combined with material obtained via filtration (568 mg): MS (M+H) 414.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. filtrationthe resulting white solid was collected by vacuum filtration
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo
  7. custompurified
  8. customobtained via filtration (568 mg)

Quellen und Nachweise

ORD-Eintrag
ord-d9b9795b37794f49848c23bd5db2cdd3
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359300B2

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