Hydroxyamine hydrochloride → HCID 76619672, compound

HRID 1684872Notes

Reaction equation

HRID 1684872 reaction equation
CC([O-])=O.[Na+].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=O)[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1.Cl.[OH:19][NH2:20]>O.CCO>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[N:20][OH:19])[CH2:12][CH2:13][O:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 76619672HCID 76619672, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

NaOAc (3.78 g, 46.2 mmol) in H2O (30 mL) was added to a soln of 7-bromo 4-chromanone (3.5 g, 15.4 mmol) and hydroxyl-amine hydrochloride (1.75 g, 23.1 mmol) in EtOH (70 ml). The reaction was heated at reflux for 2 h, cooled to room temperature, and concentrated. The residue was diluted with H2O and a precipitate was filtered to give 7-bromochroman-4-one oxime obtained as the needle like crystals 3.5 g (98%). LCMS 244 (M+2H) RT=1.7 min (Condition 2); 1H NMR (DMSO-d6) 11.37 (s, OH, 1H), 7.76-7.70 (d, 1H), 7.09-7.13 (d, 2H), 4.16-4.20 (t, 2H), 2.79-2.83 (t, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. additionThe residue was diluted with H2O
  5. filtrationa precipitate was filtered

Sources & evidence

ORD record
ord-bdc1ba9cd7b5447bb2e9f75fe667675e
Source dataset
uspto-grants-2012_04
Patent number
US08147818B2

Reaction notes

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