Ethanolamine → 3-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

HRID 14461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14461
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13](F)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:31]([CH2:33][NH2:34])[OH:32]>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([F:20])[C:13]([NH:34][CH2:33][CH2:31][OH:32])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:21]([CH3:22])[CH3:23])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 68704522HCID 68704522, Verbindung

Produkt 1

HCID 687043963-(4-Chlorophenyl)-8-fluoro-7-(2-hydroxyethylamino)-2-isopropyl-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A stirred solution of 3-(4-chlorophenyl)-7,8-difluoro-2-isopropyl-chromen-4-one (3.94 g, 11.8 mmol), triethylamine (2.4 g, 3.2 ml, 23.6 mmol, 2 eq.) and ethanolamine (0.72 g, 0.71 ml, 11.8 mmol, 1 eq.) in N,N-dimethylacetamide (200 ml) is heated at 150° C. overnight. The reaction mixture is allowed to cool to room temperature and the solvent is removed by evaporation in vacuo. The residue is dissolved in ethyl acetate and washed with 2M HCl solution. The organic layer is washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown oil. The oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6) to afford the title compound.

Aufarbeitung

  1. customthe solvent is removed by evaporation in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 2M HCl solution
  4. washThe organic layer is washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customto afford a brown oil
  9. customThe oil is purified by flash chromatography (cyclohexane/ethyl acetate=9:1 to 4:6)

Quellen und Nachweise

ORD-Eintrag
ord-53cb518bd0a54f4e82fd9274a2a555d0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732435B2

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