Hydroxyamine hydrochloride → 2,4-Dimethyl-3-(1-hydroxyiminoethyl)-5-(4-pyridyl)furan

HRID 2121706Notes

Reaction equation

HRID 2121706 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[O:6][C:5]=1[CH3:16])(=O)[CH3:2].Cl.[NH2:18][OH:19]>CCO.N1C=CC=CC=1>[CH3:16][C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:8]([CH3:9])[C:4]=1[C:1](=[N:18][OH:19])[CH3:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 98372883-Acetyl-2,4-dimethyl-5-(4-pyridyl)furan

Product 1

HCID 734106212,4-Dimethyl-3-(1-hydroxyiminoethyl)-5-(4-pyridyl)furanYield 84.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-acetyl-2,4-dimethyl-5-(4-pyridyl)furan (0.5 g, 2.33 mM) in EtOH (10 mL) and pyridine (2 mL) was added hydroxylamine hydrochloride (0.2 g, 2.79 mM) at room temperature. After stirring overnight, volatiles were removed by evaporation. Ethyl acetate (100 mL) and water (70 mL) were added, and partitioned. The organic layer was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The resulting solid was triturated to give the subtitle compound (0.45 g, 84% yield).

Workup

  1. customvolatiles were removed by evaporation
  2. additionEthyl acetate (100 mL) and water (70 mL) were added
  3. custompartitioned
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was triturated

Sources & evidence

ORD record
ord-7bf45eb3799e41c290aa16ee3ecc31e2
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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