Methanol → N-[1-(Furan-2-yl)propylidene]hydroxylamine

HRID 2388199Notes

Reaction equation

HRID 2388199 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].CO.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](=O)[CH2:17][CH3:18]>O>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](=[N:2][OH:3])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 766621-(2-Furyl)propan-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 71339142N-[1-(Furan-2-yl)propylidene]hydroxylamineYield 100.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (3.3 g, 47.8 mmol) and sodium acetate (3.9 g, 47.8 mmol) were added to 20 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. 1-(Furan-2-yl)propan-1-one (5.4 g, 43.5 mmol) was added and the mixture was stirred at room temperature for 20 hours. Water (20 mL) was added and the product was extracted with EtOAc and the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. The solvent was evaporated in vacuo to give 6.1 g of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. extractionthe product was extracted with EtOAc
  3. washthe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c70a4ca1491d4e888e96543ab1faec15
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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