1,3-Butanedione, 1-(2-furanyl)- → 3-Amino-1-(2-furanyl)-2-buten-1-one

HRID 1906166

Reaction equation

HRID 1906166 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:11])[CH2:7][C:8](=O)[CH3:9].C([O-])(=O)C.[NH4+:16]>C1(C)C=CC=CC=1>[NH2:16][C:8]([CH3:9])=[CH:7][C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 121681,3-Butanedione, 1-(2-furanyl)-HCID 517165Ammonium Acetate

Product 1

HCID 704481453-Amino-1-(2-furanyl)-2-buten-1-oneYield 48.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The intermediate 3-amino-1-(2-furanyl)-2-buten-1-one was prepared as follows: A mixture containing 165 g of 1-(2-furanyl)-1,3-butanedione, 700 ml of toluene and 200 g of ammonium acetate was azeotroped for six hours, cooled and concentrated to dryness in vacuo. The residue was dissolved in isopropyl alcohol, the solution treated with decolorizing charcoal and filtered, and the filtrate concentrated to remove the solvent. The remaining residue was recrystallized from ether-ethanol and dried at room temperature to yield 80.2 g of 3-amino-1-(2-furanyl)-2-buten-1-one, m.p. 128°-130° C. Another 33.4 g of the product, m.p. 128°-130° C. was collected by concentrating the mother liquor and extracting the product with ether.

Workup

  1. customThe intermediate 3-amino-1-(2-furanyl)-2-buten-1-one was prepared
  2. customwas azeotroped for six hours
  3. temperaturecooled
  4. concentrationconcentrated to dryness in vacuo
  5. dissolutionThe residue was dissolved in isopropyl alcohol
  6. additionthe solution treated with decolorizing charcoal
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customto remove the solvent
  10. customThe remaining residue was recrystallized from ether-ethanol
  11. customdried at room temperature

Sources & evidence

ORD record
ord-1c1a73a4389c4affa6a806ad68320814
Source dataset
uspto-grants-1987_03
Patent number
US04650806

Linked notes

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