Hydrazine hydrate (1:1) → 4-(5-methyl-4-phenyl-1H-pyrazol-3-yl)benzene-1,3-diol

HRID 1296918Notes

Reaction equation

HRID 1296918 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1.O.[NH2:21][NH2:22]>C(O)C>[CH3:12][C:8]1[NH:22][N:21]=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:11][C:10]=2[OH:9])[C:7]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53809767-Hydroxy-2-methyl-3-phenyl-4H-chromen-4-one

Product 1

HCID 9369204-(5-methyl-4-phenyl-1H-pyrazol-3-yl)benzene-1,3-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compounds was synthesised in the same manner as described above. 7-Hydroxy-2-methyl-3-phenyl-chromen-4-one (0.5 g, 1.70 mmol), hydrazine hydrate (5 ml), ethanol (10 ml). The quenched solution was extracted into ethyl acetate, washed (water), dried (MgSO4), and the solvent removed under vacuum to give a yellow oil which was purified by column chromatography to give 4-(5-Methyl-4-phenyl-1H-pyrazol-3-yl)-benzene-1,3-diol as an off white solid (0.37 g, 88%); Rf 0.7 Cf SM 0.8 ethyl acetate/hexane (80/20).

Workup

  1. customThis compounds was synthesised in the same manner
  2. extractionThe quenched solution was extracted into ethyl acetate
  3. washwashed (water)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under vacuum
  6. customto give a yellow oil which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-403181738b0a42d7b1a9af64ac077139
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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