Hydroxyamine hydrochloride → 5-Hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-4-carbaldehyde oxime

HRID 1836007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836007
[OH:1][C:2]1[C:17]([CH:18]=O)=[C:6]2[CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)[O:9][C:5]2=[C:4]([O:20][CH3:21])[CH:3]=1.[NH2:22][OH:23].Cl>CCO.N1C(=O)CC[C@H]1C(O)=O>[OH:1][C:2]1[C:17]([CH:18]=[N:22][OH:23])=[C:6]2[CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)[O:9][C:5]2=[C:4]([O:20][CH3:21])[CH:3]=1

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 101494185-Hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-4-carbaldehyde

Produkt 1

HCID 1363978535-Hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-4-carbaldehyde oxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 131724523EtOH PyrLösungsmittel

Versuchsvorschrift

Compound 71 (0.029 g, 0.1 mmol) in EtOH/Pyr (1 mL/0.5 mL) was treated with NH2OH HCl (0.040 g, 0.58 mmol) and the mixture heated briefly to reflux (approximately 5 minutes) and allowed to cool and then the solution was partitioned between EtOAc and 2 N HCl aq and the organic layer was then washed with NaHCO3 aq, brine, dried over MgSO4, filtered, concentrated and triturated with CH2Cl2 to render 29 mg of the desired oxime: Mp=205° C. (dec.); 1H NMR (DMSO-d6) δ 11.1 (s, 1 H), 10.0 (s, 1 H), 9.90 (s, 1H), 8.53 (s, 1 H), 7.65 (d, 2 H, J=8.6 Hz), 7.39 (s, 1 H), 6.88 (d, 2 H, J=8.7 Hz), 6.47 (s, 1 H), 3.94 (s, 3 H); MS 300 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture heated briefly
  2. temperatureto reflux (approximately 5 minutes)
  3. temperatureto cool
  4. customthe solution was partitioned between EtOAc and 2 N HCl aq
  5. washthe organic layer was then washed with NaHCO3 aq, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customtriturated with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-20b8c6815d4f4cea93654439df4d2fab
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774248B2

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