Citric Acid → N,5-Dimethoxy-N-methyl-1H-indole-2-carboxamide

HRID 31548

Reaktionsgleichung

Reaktionsgleichung von HRID 31548
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=O)=[CH:6]2.Cl.[CH3:16][NH:17][O:18][CH3:19].CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:18][N:17]([CH3:16])[C:12]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)=[O:14]

Komponenten

9

Edukt 6

HCID 311Citric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 204015-Methoxyindole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 23003326N,5-Dimethoxy-N-methyl-1H-indole-2-carboxamideAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxyindole-2-carboxylic acid (5 g, 26 mmol) in N,N-dimethylformamide were added N,O-dimethylhydroxyamine hydrochloride (3.04 g, 31.2 mmol) and WSC (5.98 g, 31.2 mmol), 1-hydroxybenzotriazole (4.21 g, 31.2 mmol) and triethylamine (7.24 ml, 52 mmol), and the mixture was stirred for 6 hours. To this reaction solution were added ethyl acetate and 10% (Wt) citric acid, and the organic layer was extracted. The aqueous layer was extracted twice with ethyl acetate, and combined with the organic layer. The mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated saline. The organic layer was separated, and dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (4.5 g, 70%).

Aufarbeitung

  1. extractionthe organic layer was extracted
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated saline
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7b23b6dc3dc64421a1c074c6a21315e7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425642B2

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