Sodium Carbonate → 3-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-one

HRID 270694

Reaktionsgleichung

Reaktionsgleichung von HRID 270694
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH:22]=O)=[O:14].C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:14])[NH:15][C:16]2[C:17]([CH:22]=1)=[CH:18][N:19]=[CH:20][CH:21]=2

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 598338592-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide

Produkt 1

HCID 598339183-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-oneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide (5.0 g, 14.12 mmol) and Na2CO3 (2.5 g) in MeOH (300 mL) is heated for 15 minutes at 70° C. After filtration of the reaction mixture, the solvent is removed by concentration to give crude product, which is purified by flash silica gel column elute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (93/7%) to give the titled intermediate as a solid (3.75 g, 77.7%).

Aufarbeitung

  1. filtrationAfter filtration of the reaction mixture
  2. customthe solvent is removed by concentration
  3. customto give crude product, which
  4. customis purified by flash silica gel column
  5. washelute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (93/7%)

Quellen und Nachweise

ORD-Eintrag
ord-4b99fbcd4e8446b9be2e524b54b79be4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

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