Chromanone → Chroman-4-one oxime

HRID 918889Notes

Reaction equation

HRID 918889 reaction equation
C([O-])(=O)C.[Na+].[O:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=O)[CH2:8][CH2:7]1.Cl.[NH2:18][OH:19]>CCO.CCOC(C)=O>[O:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)/[C:9](=[N:18]/[OH:19])/[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 68110ChromanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9673039Chroman-4-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Sodium acetate (503.852 mg, 6.14 mmol) was added to a stirred solution of 4-chromanone ([CAS491-37-2], 700 mg, 4.73 mmol) and hydroxylamine hydrochloride ([CAS5470-11-1], 426.808 mg, 6.14 mmol) in EtOH (31 mL). The mixture was stirred at 80° C. for 16 h. The mixture was cooled to RT, diluted with EtOAc, and washed with water. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo to yield I-36 (727.7 mg, 93%) as a white solid, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield I-36 (727.7 mg, 93%) as a white solid, which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-01ce3fc98254464aa627e37a67d6019a
Source dataset
uspto-grants-2016_03
Patent number
US09271967B2

Reaction notes

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