Chromanone → Chroman-4-one oxime

HRID 1612205Notes

Reaction equation

HRID 1612205 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.C([O-])(=O)C.[Na+].Cl.[OH:18][NH2:19].C(=O)(O)[O-].[Na+]>C(O)C.O>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:4](=[N:19]/[OH:18])/[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 68110ChromanoneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 9673039Chroman-4-one oximeYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,3-dihydro-4H-chromen-4-one (3.00 g) in ethanol (15 ml)/water (3 ml) was added sodium acetate (6.64 g) and hydroxyl amine hydrochloride (5.52 g). The reaction mixture was heated at 70° C. for 1 h, poured into saturated sodium bicarbonate (50 ml), extracted methylene chloride (3×50 ml), dried MgSO4, filtered and concentrated to provide the title compound as a solid (3.22 g, 99%): 1H NMR (300 MHz, CDCl3) δ) 7.86, 7.28, 7.00-6.91, 4.27, 3.02; HRMS (FAB) calcd for C9H9NO2+H 164.0712, found 164.0703. Anal. Calcd for C9H9NO2: C, 66.25; H, 5.56; N, 8.58. Found: C, 66.21; H, 5.58; N, 8.57.

Workup

  1. extractionextracted methylene chloride (3×50 ml), dried MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c05148d6cde44d12a5e4c790bbd5816d
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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