Hydrazine hydrate (1:1) → 4-[4-(2-Bromo-phenyl)-5-methyl-1H-pyrazol-3-yl]-6-chloro-benzene-1,3-diol

HRID 1296921Notes

Reaction equation

HRID 1296921 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17](=O)[C:16]2[C:11](=[CH:12][C:13]([OH:20])=[C:14]([Cl:19])[CH:15]=2)[O:10][C:9]=1[CH3:21].O.[NH2:23][NH2:24]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([C:16]2[CH:15]=[C:14]([Cl:19])[C:13]([OH:20])=[CH:12][C:11]=2[OH:10])=[N:23][NH:24][C:9]=1[CH3:21]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 589135013-(2-Bromo-phenyl)-6-chloro-7-hydroxy-2-methyl-chromen-4-one

Product 1

HCID 1360492904-[4-(2-Bromo-phenyl)-5-methyl-1H-pyrazol-3-yl]-6-chloro-benzene-1,3-diol

Procedure

This compounds was synthesised in the same manner as described above. 3-(2-Bromo-phenyl)-6-chloro-7-hydroxy-2-methyl-chromen-4-one (2.5 g, 6.9 mmol), Hydrazine hydrate (10 ml). 4-[4-(2-Bromo-phenyl)-5-methyl-1H-pyrazol-3-yl]-6-chloro-benzene-1,3-diol precipitated out as an off white solid (0.53 g, 20.2%); Rf 0.5 cf SM 0.85 [ethyl acetate/petroleum ether 40–60° C. (80/20)].

Workup

  1. customThis compounds was synthesised in the same manner
  2. custom4-[4-(2-Bromo-phenyl)-5-methyl-1H-pyrazol-3-yl]-6-chloro-benzene-1,3-diol precipitated out as an off white solid (0.53 g, 20.2%)
  3. customcf SM 0.85 [ethyl acetate/petroleum ether 40–60° C. (80/20)]

Sources & evidence

ORD record
ord-123ac36d5e5e4027b7501d899caf7b90
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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