Hydrazine hydrate (1:1) → 4-Amino-3,5-dimethylphenol

HRID 1885661Notes

Reaction equation

HRID 1885661 reaction equation
[CH3:1][C:2]1[C:3](N=NC2C=CC=CC=2O)=[C:4]([OH:15])[CH:5]=[C:6]([CH3:14])[C:7]=1C1C=CC=CC=1.O.[NH2:26]N>CO.[Ni]>[CH3:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[C:6]([CH3:14])[C:7]=1[NH2:26]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 136403395HCID 136403395, compound

Product 1

HCID 765434-Amino-3,5-dimethylphenolYield 60%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3,5-Dimethyl-4-phenylazophenol (132.0 g, 0.583 mol) was dissolved in methanol (500 mL) and pure (100%) hydrazine hydrate (113 mL, 2.33 mol), and Raney nickel [50% slurry in water (Aldrich), (2.5 mL)] was added to give an exothermic reaction. The mixture was stirred for one hour at ambient temperature and then heated to gentle reflux for three hours. The solution was filtered hot and cooled to room temperature. The crystals which formed were collected by filtration and dried to afford 3,5-dimethyl-4-aminophenol (42.4 g, 60% yield) as a white solid; m.p. 180.5-182.5; 1H-NMR (DMF-d7). δ 2.10 (s, 6H, CH3), 5.32 (s, 2H, NH2), 5.32 (s, 1H, OH), 6.45 (s, 2H, aromatic).

Workup

  1. customto give
  2. customan exothermic reaction
  3. temperatureheated
  4. temperatureto gentle reflux for three hours
  5. filtrationThe solution was filtered hot
  6. temperaturecooled to room temperature
  7. customThe crystals which formed
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c00677ae18d841a2b5ad3a070fc364c4
Source dataset
uspto-grants-1992_09
Patent number
US05145942

Reaction notes

Loading…