Hydrazine hydrate (1:1) → HCID 18406882, compound

HRID 1016393Notes

Reaction equation

HRID 1016393 reaction equation
O[C:2]1[CH:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:7])[O:5][CH:6]=1.O.[NH2:15][NH2:16]>C(O)C>[OH:5][CH2:6][C:2]1[N:16]=[N:15][C:4](=[O:7])[C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18406888HCID 18406888, compound

Product 1

HCID 18406882HCID 18406882, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Hydroxy-3-phenyl-2-furanone (3 g, 0.017 mol) was dissolved in ethanol (17 ml) with hydrazine hydrate (0.83 ml, 0.017 mol) and heated at reflux for 10 days (over this time the solvent evaporated). The residue was redissolved in ethanol (17 ml) and heated at reflux then allowed to cool and the solid that crystallised out was collected by filtration (2.2 g, mp=173° C.). Data for the title compound: 1H NMR (360 MHz, d6-DMSO) δ 4.45 (1H, s), 5.31 (1H, s), 7.14 (1H, t, J=7.3 Hz), 7.34 (2H, t, J=7.3 Hz), 7.55 (2H, d, J=7.3 Hz); MS (ES+) m/e 191 [MH]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 days (over this time the solvent
  3. customevaporated)
  4. dissolutionThe residue was redissolved in ethanol (17 ml)
  5. temperatureheated
  6. temperatureat reflux
  7. temperatureto cool
  8. customthe solid that crystallised out
  9. filtrationwas collected by filtration (2.2 g, mp=173° C.)

Sources & evidence

ORD record
ord-c540584055624397852a5ebe36934050
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

Loading…