Methyl iodide → 3-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

HRID 270695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270695
[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:22])[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][N:18]=[CH:17][CH:16]=2.I[CH3:24]>CN(C=O)C.CCOC(C)=O>[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:22])[N:14]([CH3:24])[C:15]2[C:20]([CH:21]=1)=[CH:19][N:18]=[CH:17][CH:16]=2

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 598339183-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-one

Produkt 1

HCID 598338673-(2,6-dichloro-3-nitro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-oneAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-one (2.0 g, 5.95 mmol) in DMF (50 mL) is added HNa (286 mg, 60%, 7.14 mmol) and IMe (0.5 mL, 8.03 mmol) at 0° C. The mixture is stirred for two hours at 0° C., diluted with EtOAc (300 ml) and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column elute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3)(98.5/1.5) to give the titled intermediate as a solid (1.67 g, 80.3%).

Aufarbeitung

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by flash silica gel column
  7. washelute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3)(98.5/1.5)

Quellen und Nachweise

ORD-Eintrag
ord-9042f78d2d3545e090ceb2ee57104ec6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

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