Water → 1-(4-Methoxyphenyl)-2-phenylhydrazine

HRID 23568Notes

Reaction equation

HRID 23568 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.O>C(O)C.[NH4+].[Cl-].[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 962WaterHCID 169664-Methoxyazobenzene

Product 1

HCID 123261241-(4-Methoxyphenyl)-2-phenylhydrazineYield 100.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 25517Ammonium ChlorideSolvent2×

Procedure

Zinc powder (10.0 g; 0.15 mol) was added to a stirred mixture of 4-methoxyazobenzene (4.24 g; 20.0 mmol) in 96% ethanol (75 ml) and saturated NH4Cl solution (2.0 ml) at 0° C. (bath temperature). Two more portions of saturated NH4Cl solution (2.0 ml) were added at 1.5 h intervals. The yellowish solution was poured into cold water (100 ml) and filtered. The residue was extracted with methylene chloride (5×50 ml). The combined aqueous phases were extracted with methylene chloride (3×25 ml). The combined organic solutions were,dried (Na2SO4), filtered and evaporated to give 4.3 g crude 1-(4-methoxyphenyl)-2-phenylhydrazine as a reddish oil.

Workup

  1. filtrationfiltered
  2. extractionThe residue was extracted with methylene chloride (5×50 ml)
  3. extractionThe combined aqueous phases were extracted with methylene chloride (3×25 ml)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-153d55fc25eb41fba592f2a192e60356
Source dataset
uspto-grants-2005_02
Patent number
US06852749B1

Reaction notes

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