Hydrazine hydrate (1:1) → HCID 178515922, compound

HRID 1296895Notes

Reaction equation

HRID 1296895 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>C(O)C>[C:12]1([C:7]2[C:6]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:11][C:10]=3[OH:9])=[N:20][NH:21][CH:8]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53768917-Hydroxyisoflavone

Product 1

HCID 178515922HCID 178515922, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

7-Hydroxy-3-phenyl-chromen-4-one (0.2 g, 0.84 mmol) was dissolved in ethanol (5 ml) and heated to ˜60° C. Hydrazine hydrate (5 ml) was added, and the solution refluxed until no starting material was visible by TLC (45 mins). After this time the majority of the ethanol was remove under vacuum and the residue quenched with cold water. The residue was extracted into ethyl acetate, washed (water), and the solvent removed under vacuum to give 4-(4-Phenyl-1H-pyrazol-3-yl)-benzene-1,3-diol as a white solid (0.17 g, 80.3%); Rf 0.65 ethyl acetate/hexane (70/30)].

Workup

  1. temperaturethe solution refluxed until no starting material
  2. customwas visible by TLC (45 mins)
  3. customAfter this time the majority of the ethanol was remove under vacuum
  4. customthe residue quenched with cold water
  5. extractionThe residue was extracted into ethyl acetate
  6. washwashed (water)
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ded1de0a5b8343f382c8dc9f7bbba02e
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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