Hydroxyamine hydrochloride → HCID 19759217, compound

HRID 248397Notes

Reaction equation

HRID 248397 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[CH:13]=O)=[CH:4][CH:3]=1.Cl.[NH2:16]O.C([O-])(=O)C.[Na+]>C(O)C.C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[C:13]#[N:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate2×HCID 19759408HCID 19759408, compound

Product 1

HCID 19759217HCID 19759217, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(4-methylphenyl)furane-2-carbaldehyde (1.0 g), hydroxylamine hydrochloride (560 mg), and sodium acetate (660 mg) in 60% aqueous ethanol (10 ml) was stirred for one and half hours at 65° C. The mixture was concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried, and concentrated in vacuo to give a yellow solid. A mixture of the solid and sodium acetate (56 mg) in acetic anhydride (10.5 ml) was refluxed for 5 hours and then evaporated in vacuo. The residue was purified by column chromatography on silica gel (elution by n-hexane/ethyl acetate=15/1) to yield 3-(4-methylphenyl)furane-2-carbonitrile (884 mg) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid
  7. temperaturewas refluxed for 5 hours
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (elution by n-hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-7d9dd286b04e47669a1e05feef04a2f4
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

Loading…