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

HRID 1836007Notes

Reaction equation

HRID 1836007 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 131724523EtOH PyrSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-20b8c6815d4f4cea93654439df4d2fab
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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