Triethylamine → 5-(Dimethylaminomethylenamino)-3-(4-quinolylmethylen)-2-oxindole

HRID 1075679

Reaktionsgleichung

Reaktionsgleichung von HRID 1075679
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.[CH2:23]([N:25]([CH2:28]C)[CH2:26]C)C>C1COCC1.ClCCl>[CH3:23][N:25]([CH:28]=[N:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1)[CH3:26]

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

Produkt 1

HCID 540938175-(Dimethylaminomethylenamino)-3-(4-quinolylmethylen)-2-oxindoleAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-3-(4-quinolylmethylen)-2-oxindole (287 mg, 1 mmol) and triethylamine (121 mg, 1.2 mmol) in THF (20 ml) was added portionwise at, 0° C. chlorodimethyl-formimminium chloride (154 mg, 1.2 mmol) and the stirring was continued at room temperature for 1 h. Then the reaction mixture was diluted with dichloromethane, the organic layer washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was chromatographed on silica gel (eluant ethyl acetate/methanol 1:1) to give pure title compound in 60% yield (205 mg).

Aufarbeitung

  1. washthe organic layer washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was chromatographed on silica gel (eluant ethyl acetate/methanol 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b987982202434f22b89e60cb640d9d6a
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05905149

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