Hydrazine hydrate (1:1) → HCID 136049316, compound

HRID 1296952Notes

Reaction equation

HRID 1296952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[OH:12])[O:8][C:7]([CH3:14])=[C:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH:5]2O.O.[NH2:25][NH2:26]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:6]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[C:7]([CH3:14])[NH:26][N:25]=2)[C:9]([OH:8])=[C:10]([CH3:13])[C:11]=1[OH:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58913661HCID 58913661, compound

Product 1

HCID 136049316HCID 136049316, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-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 (neat DCM). The yellow oil was then triturated with ether:hexane to give 4-chloro-6-[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 (neat DCM)
  5. customThe yellow oil was then triturated with ether

Sources & evidence

ORD record
ord-69a46ae2dd7e45238698ffcb205b41c9
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

Loading…