(4-Methoxyphenyl)hydrazine → HCID 15480880, compound

HRID 1596595Notes

Reaction equation

HRID 1596595 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=[CH:5][CH:4]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1>C(O)C>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[N:31]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 875961,3-Bis(4-methoxyphenyl)-1,3-propanedione

Product 1

HCID 15480880HCID 15480880, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the 1,3-diketone obtained in step 1 (1.0 equiv.), 4-methoxyphenyl hydrazine (1.5 equiv.) conc. HCl aq. (catalytic amount) and ethanol was heated to reflux overnight. Cooled to rt and removed solvent in vacuo. Water and ethyl acetate were added. The organic layer was separated, washed with dil. HCl, brine, dried, filtered and the solvent was concentrated in vacuo to give the product 1-[1,5-bis(4-methoxyphenyl)pyrazol-3-yl]-4-methoxybenzene.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customremoved solvent in vacuo
  4. additionWater and ethyl acetate were added
  5. customThe organic layer was separated
  6. washwashed with dil. HCl, brine
  7. customdried
  8. filtrationfiltered
  9. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-f948ae306b244f3b88afecc6da6b02be
Source dataset
uspto-grants-2001_09
Patent number
US06291505B1

Reaction notes

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