Hydroxyamine hydrochloride → HCID 85613806, compound

HRID 466186

Reaction equation

HRID 466186 reaction equation
[C:1]([C:4]1[CH2:5][O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][C:8]=2[CH:9]=1)(=O)[CH3:2].Cl.[NH2:22][OH:23]>CCO.N1C=CC=CC=1>[C:1](=[N:22][OH:23])([C:4]1[CH2:5][O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][C:8]=2[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 14971313HCID 14971313, compound

Product 1

HCID 85613806HCID 85613806, compound

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

The ketone (2.53 g, 9.5 mmol) is dissolved in 90 ml of an EtOH/pyridine mixture (1:1), and treated with hydroxylamine hydrochloride (0.99 g, 14.3 mmol). The mixture is stirred for 2 days. The reaction mixture is partitioned between ether and water, and the aqueous layer is extracted twice with ether. The combined organic layer is then washed twice with 2N HCl and water, dried (MgSO4), and evaporated. The residue is purified by flash chromatography (10% EtOAc/hexane) to give 3-acetyl-6-phenoxy-2H-1-benzopyran oxime as a crystalline solid.

Workup

  1. customThe reaction mixture is partitioned between ether and water
  2. extractionthe aqueous layer is extracted twice with ether
  3. washThe combined organic layer is then washed twice with 2N HCl and water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatography (10% EtOAc/hexane)

Sources & evidence

ORD record
ord-0152ccd687c04e58ac7554e776404ca2
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Linked notes

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