Hydroxyamine hydrochloride → HCID 85960732, compound

HRID 532125Notes

Reaction equation

HRID 532125 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=O.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[N:15][OH:16]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 46121686-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 85960732HCID 85960732, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

5.2 g (29.2 mmol) of 6-methoxychroman-4-one were dissolved in ethanol and 2.53 g (36.5 mmol) hydroxylamine hydrochloride and 2.99 g (36.5 mmol) sodium acetate dissolved in 10 ml of water were added. The mixture was stirred at 65° C. for 1.5 hours. The mixture was allowed to cool to room temperature and concentrated. The residue was dissolved in methyl-tert-butylether. The organic phase was washed with water, dried over MgSO4 and concentrated to give 5.6 g (29.4 mmol, quant.) of crude product, which was directly used in the next step.

Workup

  1. additionwere added
  2. temperatureto cool to room temperature
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methyl-tert-butylether
  5. washThe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give 5.6 g (29.4 mmol, quant.) of crude product, which

Sources & evidence

ORD record
ord-ac88c1d315124f74bf323645dd536750
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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