Water → 1-{4-[4-(2-Hydroxyethyl)anilino]-3-nitrophenyl}ethanone

HRID 724073

Reaktionsgleichung

Reaktionsgleichung von HRID 724073
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+].O>CN(C=O)C>[OH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])=[CH:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 669044-Aminophenethyl alcoholHCID 795964'-Chloro-3'-nitroacetophenoneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 218759851-{4-[4-(2-Hydroxyethyl)anilino]-3-nitrophenyl}ethanoneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-acetylnitrobenzene (Oelschlaeger, H.; Schreiber, O. Liebigs Ann. Chem., 1961, 641, 81., 2 g, 10 mmol), 4-aminophenylethyl alcohol (1.64 g, 12 mmol) and NaHCO3 (1 g, 12 mmol) in DMF (60 mL) was heated at 150° C. for 3 h. After cooling, the mixture was poured into water (100 mL) and extracted with ethyl acetate (300 mL). The organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL), then dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 1.36 g (45%) of the title compound as an orange oil; 1H-NMR (CDCl3) δ 9.83 (1H, br.s), 8.20 (1H, d, J=2.1 Hz), 7.94 (1H, dd, J=2.1 Hz, 9.3 Hz), 7.34 (2H, d, J=8.2 Hz), 7.24 (2H, d, J=8.2 Hz), 7.16 (1H, d, J=9.3 Hz), 3.91 (2H, t, J=6.6 Hz), 2.92 (2H, t, J=6.6 Hz), 2.57 (3H, s).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with 2N aqueous NaOH (100 mL) and brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-1928c56af774416dbbf55fd909b475a9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141580B2

Verknüpfte Notizen

Wird geladen…