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

HRID 1296948Notes

Reaction equation

HRID 1296948 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18](O)[C:17]3[C:12](=[C:13]([CH3:21])[C:14]([OH:20])=[CH:15][CH:16]=3)[O:11][C:10]=2[CH3:22])=[CH:5][CH:4]=1.O.[NH2:24][NH2:25]>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:17]3[CH:16]=[CH:15][C:14]([OH:20])=[C:13]([CH3:21])[C:12]=3[OH:11])=[N:24][NH:25][C:10]=2[CH3:22])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 589136083-(4-methoxy-phenyl)-2,8-dimethyl-4H-chromene-4,7-diol

Product 1

HCID 1360492764-[4-(4-methoxy-phenyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-benzene-1,3-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Methoxy-phenyl)-2,8-dimethyl-4H-chromene-4,7-diol (1 eq) was taken up in a 1:1 solution of EtOH:Hydrazine hydrate and heated under microwave conditions (120° C., 300 sec). The solution was concentrated in vacuo, residue quenched with cold water, extracted with ethyl acetate and purified by flash chromatography (1% MeOH-DCM). The yellow oil was then triturated with ether:hexane to give 4-[4-(4-methoxy-phenyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-benzene-1,3-diol as a solid.

Workup

  1. concentrationThe solution was concentrated in vacuo, residue
  2. customquenched with cold water
  3. extractionextracted with ethyl acetate
  4. custompurified by flash chromatography (1% MeOH-DCM)
  5. customThe yellow oil was then triturated with ether

Sources & evidence

ORD record
ord-42368abd00824acea291566001c6be77
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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