Hydrochloric Acid → 4-Methoxy-1-[5-(4-methoxyphenyl)4benzylpyrazol-3-yl]benzene

HRID 1596592Notes

Reaction equation

HRID 1596592 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[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.[NH2:29][NH2:30].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[NH:30][N:29]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 227255101,3-Bis(4-methoxyphenyl)-2-benzylpropane-1,3-dione

Product 1

HCID 227256094-Methoxy-1-[5-(4-methoxyphenyl)4benzylpyrazol-3-yl]benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the 1,3-diketone obtained in step 1 (1.0 equiv.), hydrazine (3.0 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 4-methoxy-1-[5-(4-methoxyphenyl)4benzylpyrazol-3-yl]benzene.

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-54a2090908e84c3db316bb16fa149534
Source dataset
uspto-grants-2001_09
Patent number
US06291505B1

Reaction notes

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