Chromanone → 4H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

HRID 1269447Notes

Reaction equation

HRID 1269447 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.Cl.[NH2:13][OH:14].CC([O-])=O.[Na+]>CCO.O>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:13][OH:14])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 68110ChromanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-chromanone (10.00 g, 67.50 mmol) and hydroxylamine hydrochloride (7.04 g, 101 mmol) in EtOH (100 ml) was added a solution of NaOAc (16.61 g, 202.5 mmol) in H2O (30 mL). The reaction was heated to reflux for 2 h. The mixture was cooled to RT and concentrated in vacuo. The residue was diluted with H2O and acidified with 1N HCl. The aqueous was extracted with EtOAc until tlc analysis showed no evidence of title compound in the aqueous layer. The combined organics were dried with MgSO4 and concentrated in vacuo to furnish the crude title compound which was used without further purification. MS (APCI pos) 164 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with H2O
  5. extractionThe aqueous was extracted with EtOAc until tlc analysis
  6. dry with materialThe combined organics were dried with MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00c40a69e5af4b738ca81e10457f1b75
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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