2-Nitrobenzyl alcohol → 2-Aminobenzyl alcohol

HRID 971306Notes

Reaction equation

HRID 971306 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-])=O.O.NN>CO.[Pd]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 119232-Nitrobenzyl alcoholHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 214392-Aminobenzyl alcoholYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitrobenzyl alcohol (500 g, 3.2 mol) in MeOH (2.5 L) was added Pd/C (40 g) under N2 and refluxed for 30 min. Hydrazine hydrate (500 mL) was added slowly with stirring. The resulting mixture was stirred under reflux for another 2 h. The solid formed was filtered, concentrated and the crude residue was extracted with ethyl acetate (2×500 mL). The organic layer was washed with brine and dried over MgSO4. After evaporation of the solvents, 2-aminobenzyl alcohol (357 g, 89% yield) was isolated as pale yellow solid.

Workup

  1. temperaturerefluxed for 30 min
  2. stirringThe resulting mixture was stirred
  3. temperatureunder reflux for another 2 h
  4. customThe solid formed
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. extractionthe crude residue was extracted with ethyl acetate (2×500 mL)
  8. washThe organic layer was washed with brine
  9. dry with materialdried over MgSO4
  10. customAfter evaporation of the solvents

Sources & evidence

ORD record
ord-af8cd689f2e4489d96c8d3754e876e8e
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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