Hydrazine hydrate (1:1) → (2-Amino-5-ethoxyphenyl)methanol

HRID 2375415Notes

Reaction equation

HRID 2375415 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:12]([O-])=O)=[C:8]([CH2:10][OH:11])[CH:9]=1)[CH3:2].O.NN>CCO.[Pd]>[NH2:12][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][C:8]=1[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 45091604(5-Ethoxy-2-nitrophenyl)methanol

Product 1

HCID 45091061(2-Amino-5-ethoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (5-ethoxy-2-nitro-phenyl)-methanol (592 mg, 3.0 mmol) in absolute EtOH (20 mL) at rt was added 150 mg of Pd/C (Aldrich, 10 wt. % on active carbon), followed by slow addition of hydrazine hydrate (1.5 mL). The resulting reaction mixture was refluxed at 90° C. for 1 h. It was then cooled to rt, filtered through Celite, and then concentrated in vacuo to afford crude (2-amino-5-ethoxy-phenyl)-methanol as a pale yellow oil: MS (ESI) 168 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureIt was then cooled to rt
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-338acb8f1d094b2a97e573b098bdf140
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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