Hydroxylamine HCl → (NE)-N-[(2-bromo-5-phenylmethoxyphenyl)methylidene]hydroxylamine

HRID 1486863Notes

Reaction equation

HRID 1486863 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Br:17])=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[OH:19][NH3+:20].C(=O)(O)[O-].[Na+]>O.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Br:17])=[C:13](/[CH:14]=[N:20]/[OH:19])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

Product 1

HCID 118292785(NE)-N-[(2-bromo-5-phenylmethoxyphenyl)methylidene]hydroxylamineYield 87.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 5-(benzyloxy)-2-bromobenzaldehyde (29.5 g), hydroxyl ammonium chloride (7.75 g), sodium bicarbonate (9.36 g), water (30 mL), and ethanol (270 mL) was stirred overnight at room temperature. To the reaction mixture, water (150 mL) was added, and the mixture was concentrated into half the volume under reduced pressure. Then, the residue was subjected to extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was washed with hexane to obtain the title compound (27.2 g)

Workup

  1. concentrationthe mixture was concentrated into half the volume under reduced pressure
  2. extractionThen, the residue was subjected to extraction with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-cd9f44179228476f822050d000857087
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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