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

HRID 1794504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794504
[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, 1 H), 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-c036b57fca4742f6b70cabd6c8e469d2
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022733B2

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