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

HRID 2077692

Reaktionsgleichung

Reaktionsgleichung von HRID 2077692
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-111fa5e7e52b4079a060e31e05f394de
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928119B2

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