Hydroxyamine hydrochloride → HCID 136378651, compound

HRID 527525Notes

Reaction equation

HRID 527525 reaction equation
Cl.[NH2:2][OH:3].O.O.O.C([O-])(=O)C.[Na+].[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=1[C:20](=O)[CH2:21][CH3:22]>CCO.O.O>[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=1[C:20](=[N:2][OH:3])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 116223911-(2,6-dihydroxyphenyl)-propan-1-one2×HCID 23665404Sodium Acetate Trihydrate2×

Product 1

HCID 136378651HCID 136378651, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent2×

Procedure

A solution of hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 20 ml of a mixture EtOH/H2O (7/3) was added to a solution of 1-(2,6-dihydroxyphenyl)-1-propanone (Intermediate 28, 1.0 g) in 15 ml of a mixture EtOH/H2O (7/3). After refluxing and stirring under N2 overnight, additional hydroxylamine hydrochloride (510 mg, 7.3 mmol) and sodium acetate trihydrate (629 mg, 4.6 mmol) dissolved in 4.5 mL of water were added. The reaction mixture was heated at reflux an additional 3 hours. After cooling down to room temperature, the volatiles were removed. Then water was added and reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (1.05 g).

Workup

  1. temperatureAfter refluxing
  2. additionwere added
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux an additional 3 hours
  5. customthe volatiles were removed
  6. additionThen water was added
  7. customreaction mixture
  8. extractionwas extracted with ethyl acetate
  9. dry with materialThe gathered organic layers were dried over sodium sulphate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-e2ff545c5e2c4e4195ea386ccb893408
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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