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

HRID 276760Notes

Reaction equation

HRID 276760 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]>CCO>[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)2×HCID 18406888HCID 18406888, compound

Product 1

HCID 18406882HCID 18406882, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

4-Hydroxy-3-phenyl-2-furanone (5 g, 28.3 mmol) was dissolved in EtOH (60 mL) with hydrazine hydrate (6.9 mL, 0.142 mol) and heated at 140° C. in a sealed tube for 64h. Further hydrazine hydrate (4 mL, 82 mmol) was added and the mixture heated at 140° C. for another 48h. The solvent was evaporated and the residue was chromatographed on silica, eluting with 10% MeOH/DCM, followed by 20% MeOH/DCM to afford the title compound (3.62 g, 67%) as a cream solid. mp 165-168° C. 1H NMR (400 MHz, d6-DMSO) δ4.45 (2H, d, J=5.0 Hz), 5.30 (1H, t, J=5.0 Hz), 7.15 (1H, t, J=7.4 Hz), 7.33 (2H, t, J=7.6 Hz), 7.55 (2H, d, J=7.7 Hz), 9.90 (1H, brs), 11.75 (1H, brs).

Workup

  1. temperaturethe mixture heated at 140° C. for another 48h
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed on silica
  4. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-cb96b5a32cf9482bb1123b920af42ccb
Source dataset
uspto-grants-2002_03
Patent number
US06355638B1

Reaction notes

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